Carbohydrates

Section 18.
1
Biochemistry—An Overview
CARBOHYDRATES
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Copyright ©2016 Cengage Learning. All Rights Reserved. 1

Chapter 18
Chapter Outline
18.1 Biochemistry—An overview
18.2 Occurrence and functions of carbohydrates
18.3 Classification of carbohydrates
18.4 Chirality: Handedness in molecules
18.5 Stereoisomerism: Enantiomers and diastereomers
18.6 Designating handedness using Fischer projection formulas
18.7 Properties of enantiomers
18.8 Classification of monosaccharides
18.9 Biochemically important monosaccharides
18.10 Cyclic forms of monosaccharides
18.11 Haworth projection formulas
18.12 Reactions of monosaccharides
18.13 Disaccharides
18.14 Oligosaccharides
18.15 General characteristics of polysaccharides
18.16 Storage polysaccharides
18.17 Structural polysaccharides
18.18 Acidic polysaccharides
18.19 Dietary considerations and carbohydrates
18.20 Glycolipids and glycoproteins: Cell recognition
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Section 18.1
The Study of Living Things
• Biochemistry: Study of the chemical

substances found in living organisms and the
chemical interactions of these substances with
each other
• Biochemical substance: Chemical substance
found within a living organism
• Types of biochemical substances:
– Bioinorganic substances - Water and inorganic salts
– Bioorganic substances - Carbohydrates, lipids,
proteins, and nucleic acids
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Section 18.1
Bioinorganic and Bioorganic Substances
• As isolated compounds, bioinorganic and

bioorganic substances have no life in and of
themselves
– When these substances are gathered together in a
cell, their chemical interactions are able to sustain life
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Section 18.1
Q1
Biochemistry, the study of the chemical
substances of living organisms, includes the study
of:
a.carbohydrates, lipids, proteins, and salts.

b.carbohydrates, lipids, proteins, and organic salts.
c.carbohydrates, lipids, proteins, and nucleic acids.
d.carbohydrates, lipids, and proteins.
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Section 18.1
Biochemistry, the study of the chemical

substances of living organisms, includes the study
of:
a.carbohydrates, lipids, proteins, and salts.

b.carbohydrates, lipids, proteins, and organic salts.
c.carbohydrates, lipids, proteins, and nucleic acids.
d.carbohydrates, lipids, and proteins.
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Section 18.2
Occurrence and Functions of Carbohydrates
Plants and Carbohydrates
• It is estimated that more than half of all organic

carbon atoms are found in the carbohydrate
materials of plants
• Human uses for carbohydrates of the plant
kingdom extend beyond food
– Carbohydrates in the form of cotton and linen are
used as clothing
– Carbohydrates in the form of wood are used for
shelter and heating and in making paper
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Section 18.2
Carbohydrates
• Most of the matter in plants, except water, is

carbohydrate material
• Carbohydrates account for 75% of dry plant
material and are produced by photosynthesis
– Cellulose - Structural element
– Starch/glycogen - Energy reservoir
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Section 18.2
Photosynthesis
• Process in which plants produce carbohydrates

using carbon dioxide, water, and solar energy
CO 2 + H 2 O + solar energy 

Chlorophyll
Plant enzymes
 carbohydrates + O2
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Section 18.2
Functions of Carbohydrates in the Human Body
• Carbohydrate oxidation provides energy

• Carbohydrate storage, in the form of glycogen,
provides a short-term energy reserve
• Carbohydrates supply carbon atoms for the
synthesis of other biochemical substances
(proteins, lipids, and nucleic acids)
• Carbohydrates form part of the structural
framework of DNA and RNA molecules
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Section 18.2
Functions of Carbohydrates in the Human Body
• Carbohydrates linked to lipids are structural

components of cell membranes
• Carbohydrates linked to proteins function in a
variety of cell–cell and cell–molecule recognition
processes
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Section 18.2
Q2
Identify the functions of carbohydrates in the
human body.
a.They provide energy during their oxidation and a short-term

energy reserve.
b.They form part of the framework for nucleic acids and supply
carbon atoms for synthesis of other biomolecules.
c.When linked to proteins, they are involved in the cell–cell and
cell–molecule recognition process, and they function as
structural components of cell membranes when linked to lipids.
d.All the above.
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Section 18.2
Identify the functions of carbohydrates in the

human body.
a.They provide energy during their oxidation and a short-term

energy reserve.
b.They form part of the framework for nucleic acids and supply
carbon atoms for synthesis of other biomolecules.
c.When linked to proteins, they are involved in the cell–cell and
cell–molecule recognition process, and they function as
structural components of cell membranes when linked to lipids.
d.All the above.
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Section 18.3
Classification of Carbohydrates
• Empirical formula of simple carbohydrates -

– CnH2nOn or Cn(H2O)n (hydrate of C)
• n is the number of atoms
• Carbohydrate: Polyhydroxy aldehyde, ketone,
or a compound that produces such substances
upon hydrolysis
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Section 18.3
Monosaccharides
• Contain single polyhydroxy aldehyde or ketone

unit
• Cannot be broken down into simpler substances
by hydrolysis reactions
• Contain 3–7 C atoms
• 5 and 6 carbon species are more common
• Pure monosaccharides - Water soluble white,
crystalline solids
• Monosaccharides - Glucose and fructose
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Section 18.3
Disaccharides
• Contain 2 monosaccharide units covalently

bonded to each other
• Crystalline and water-soluble substances
• Common disaccharides - Table sugar (sucrose)
and milk sugar (lactose)
• Upon hydrolysis, they produce 2
monosaccharide units
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Section 18.3
Oligosaccharides
• Contain three to ten monosaccharide units

covalently bonded to each other
• Free oligosaccharides are seldom encountered
in biochemical systems
• Usually found associated with proteins and lipids
in complex molecules
– Serve structural and regulatory functions
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Section 18.3
Polysaccharides
• Contain many monosaccharide units covalently

bonded
• Number of monosaccharide units varies from a
few 100 units to 50,000 units
• Examples:
– Cellulose - Paper, cotton, wood
– Starch - Bread, pasta, potatoes, rice, corn, beans,
and peas
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Section 18.3
Q3
Carbohydrates are classified as:
a.monosaccharides, disaccharides, oligosaccharides, and

polysaccharides.
b.polyhydroxy aldehydes or ketones.
c.monosaccharides and disaccharides.
d.monosaccharides, oligosaccharides, polysaccharides,
and polyhydroxy aldehydes or ketones.
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Section 18.3
Carbohydrates are classified as:
a.monosaccharides, disaccharides, oligosaccharides, and

polysaccharides.
b.polyhydroxy aldehydes or ketones.
c.monosaccharides and disaccharides.
d.monosaccharides, oligosaccharides, polysaccharides,
and polyhydroxy aldehydes or ketones.
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Section 18.4
Chirality: Handedness in Molecules
Objects and Handedness
• Most biological molecules, including

carbohydrates, exhibit the property of
“handedness” (form of isomerism)
• Most molecules that possess “handedness” exist
in two forms:
– “Left-handed” form
– “Right-handed” form
• Related in the same manner as two hands that are
“mirror images” of each other
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Section 18.4
Mirror Images
• Mirror image: Reflection of an object in a mirror

• Classes of objects based on mirror images -
– Superimposable mirror images: Images that
coincide at all points when the images are laid upon
each other
• Achiral molecule
– Nonsuperimposable mirror images: Images where
not all points coincide when the images are laid upon
each other
• Chiral molecule (handedness)
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Section 18.4
Chirality
• Chiral center: C atom attached to 4 different
groups
• A molecule with chiral center is said to be chiral
• A C atom must have four different groups
attached to it in order to be a chiral center
• A chiral C is usually denoted by *
• Bromochloroiodomethane is a chiral organic
molecule
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Section 18.4
Q4 Practice Exercise
Indicate whether the circled carbon atom in each

of the following molecules is a chiral center.
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Section 18.4
Practice Exercise
Indicate whether the circled carbon atom in each

of the following molecules is a chiral center.
a. Not a chiral center b. Not a chiral center

c. Chiral center d. Not a chiral center
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Section 18.4
Responses of Left and Right Handed Forms of a
Molecule in a Human Body
• Both forms may be active, one may be more
active, or one may be active and other non-
active
• Example:
– Response of the body to the right-handed hormone
epinephrine is 20 times greater than responses to the
left-handed form
• Almost all monosaccharides are right handed
• Amino acids are always left handed
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Section 18.4
A carbohydrate molecule whose mirror image is

not superimposable is said to be a _____
molecule.
a.achiral
b.chiral
c.nonidentical
d.nonsuperimposable
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Section 18.4
A carbohydrate molecule whose mirror image is

not superimposable is said to be a _____
molecule.
a.achiral
b.chiral
c.nonidentical
d.nonsuperimposable
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Section 18.5
Stereoisomerism: Enantiomers and Diasterioisomers
Stereoisomers
• Isomers that have the same molecular and

structural formulas but differ in the orientation of
atoms in space
• Two types:
– Enantiomers: Stereoisomers whose molecules are
non-superimposable mirror images of each other
• Molecules with chiral center
– Diastereomers: Stereoisomers whose molecules are
not mirror images of each other
• Example: Cis-trans isomers
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Section 18.5
What feature does a carbohydrate possess that

generates stereoisomerism?
a.Presence of a chiral center

b.Presence of structural rigidity
c.Presence of three or more carbon atoms
d.Presence of an achiral center
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Section 18.5
What feature does a carbohydrate possess that

generates stereoisomerism?
a.Presence of a chiral center

b.Presence of structural rigidity
c.Presence of three or more carbon atoms
d.Presence of an achiral center
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Section 18.6
Designating Handedness Using Fischer Projection Formulas
Fischer Project Formula

• Two-dimensional structural notation for showing
the spatial arrangement of groups about chiral
centers in molecules
• According to this formula, a chiral center is
represented as the intersection of vertical and
horizontal lines
• Functional groups of high priority will be written
at the top
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Section 18.6
Tetrahedral Arrangements
• The four groups attached to the atom at the

chiral center assume a tetrahedral geometry
governed by the following conventions:
– Vertical lines from the chiral center represent bonds
to groups directed into the printed page
– Horizontal lines from the chiral center represent
bonds to groups directed out of the printed page
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Section 18.6
Fischer Project Formulas
• L and D system used to designate the

handedness of glyceraldehyde enantiomers are
shown below
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Section 18.6
• We now consider Fischer projection formulas for

the compound 2,3,4-trihydroxybutanal, a
monosaccharide with four carbons and two
chiral centers
– There are four stereoisomers for this compound and
two pairs of enantiomers
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Section 18.6
• The D,L system used to designate the

handedness of glyceraldehyde enantiomers can
be extended to other monosaccharides with
more than one chiral center
– The carbon chain is numbered starting at the carbonyl
group end of the molecule, and the highest-numbered
chiral center is used to determine D or L configuration
• Epimers: Diastereomers whose molecules differ
only in the configuration at one chiral center
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Section 18.6
What formula is used to show the two-dimensional

structure of groups around chiral centers in a
molecule?
a.Fischer projection
b.Haworth projection
c.Line angle
d.Expanded
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Section 18.6
What formula is used to show the two-dimensional

structure of groups around chiral centers in a
molecule?
a.Fischer projection
b.Haworth projection
c.Line angle
d.Expanded
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Section 18.6
How can you identify the D isomer of a

carbohydrate by looking at the Fischer projection
formula?
a.The –OH group on the chiral carbon farthest from the
carbonyl group is pointing to the right.
b.The –OH group on the chiral carbon farthest from the
carbonyl group is pointing to the left.
c.The –OH group on the chiral carbon closest to the
d.The –OH group on the chiral carbon closest to the
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Section 18.6
How can you identify the D isomer of a

carbohydrate by looking at the Fischer projection
formula?
a.The –OH group on the chiral carbon farthest from the

b.The –OH group on the chiral carbon farthest from the
carbonyl group is pointing to the left.
c.The –OH group on the chiral carbon closest to the
d.The –OH group on the chiral carbon closest to the
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Section 18.7
Properties of Enantiomers
Constitutional Isomers and Diastereomers

• Constitutional isomers differ in most chemical
and physical properties
– Have different boiling points and melting points
• Diastereomers also differ in most chemical and
physical properties
– Have different boiling points and freezing points
• In contrast, nearly all the properties of a pair of
enantiomers are the same
– Two differences:
1. Their interaction with plane polarized light
2. Their interaction with other chiral substances Return to TOC

Section 18.7
Interaction of Enantiomers with Plane-Polarized Light
• Properties of light:
– Ordinary light waves- Vibrate in all directions
– Plane polarized light waves - Vibrate only in one
direction
• Plane-polarized light is rotated clockwise (to
right) or counterclockwise (to left) when passed
through enantiomers
– Direction and extent of rotation will depend upon the
concentration of the enantiomer
– Same concentration of two enantiomers rotates light
to same extent but in opposite directions Return to TOC

Section 18.7
Figure 18.10 - Vibrational Characteristics of Ordinary
Light and Plane-Polarized Light
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Section 18.7
Dextrorotary and Levorotatory Compounds
• Enantiomers are optically active, i.e., they are

compounds that rotate the plane of polarized light
• Dextrorotatory compound: Chiral compound
that rotates light towards right (clockwise; +)
• Levorotatory compound: Chiral compound that
rotates light towards left (counterclockwise; -)
• There is no correlation between D, L and +, -
– In D and L system, the structure is viewed
– + and – can be determined using a polarimeter
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Section 18.7
Interactions Between Chiral Compounds
• Right- and left-handed baseball players cannot

use the same glove (chiral) but can use the
same hat (achiral)
– Two members of the enantiomer pair (chiral) react
differently with other chiral molecules
• Enantiomeric pairs have same solubility in
achiral solvents like ethanol and have different
solubility in chiral solvent like D-2-butanol
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Section 18.7
Interactions Between Chiral Compounds
• Enantiomers have same boiling points, melting

points, and densities
– All these are dependent upon intermolecular forces,
whereas chirality doesn’t depend on such forces
• Our body responds differently to different
enantiomers
– One may give higher rate or one may be inactive
• Example: Body response to D isomer of
hormone epinephrine is 20 times greater than
its response to L isomer
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Section 18.7
What is meant when it is said that carbohydrates

are optically active compounds?
a.A solution of carbohydrate when placed in a light beam

reflects the light back to the observer.
b.A solution of carbohydrate will rotate the plane of
polarized light.
c.A solution of carbohydrate will not rotate the plane of
polarized light.
d.Being optically active, they do not possess handedness.
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Section 18.7
What is meant when it is said that carbohydrates

are optically active compounds?
a.A solution of carbohydrate when placed in a light beam

reflects the light back to the observer.
b.A solution of carbohydrate will rotate the plane of
polarized light.
c.A solution of carbohydrate will not rotate the plane of
polarized light.
d.Being optically active, they do not possess handedness.
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Section 18.8
Classification of Monosaccharides
Monosaccharides
• Classification based on number of carbon

atoms:
– Triose - 3 carbon atoms
– Tetrose - 4 carbon atoms
– Pentoses - 5 carbon atoms
– Hexoses - 6 carbon atoms
• Classification based on functional groups:
– Aldoses: Monosaccharides with one aldehyde
group
– Ketoses: Monosaccharides with one ketone group
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Section 18.8
Monosaccharides
• Combined number of C atoms and functional

group
– Examples:
• Aldohexose - Monosaccharide with aldehyde group
and 6 C atoms
• Ketopentose - Monosaccharide with ketone group and
5 C atoms
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Section 18.8
What structural feature distinguishes an aldose

and a ketose?
a.An aldose possesses an aldehyde group, and a ketose

possesses a ketone group.
b.An aldose contains 5 carbon atoms, and a ketose
contains 6 carbon atoms.
c.An aldose possesses only –OH groups, and a ketose
possesses a carbonyl group.
d.An aldose possesses a ketone group, and a ketose
possesses an aldehyde group.
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Section 18.8
What structural feature distinguishes an aldose

and a ketose?
a.An aldose possesses an aldehyde group, and a ketose

possesses a ketone group.
b.An aldose contains 5 carbon atoms, and a ketose
contains 6 carbon atoms.
c.An aldose possesses only –OH groups, and a ketose
possesses a carbonyl group.
d.An aldose possesses a ketone group, and a ketose
possesses an aldehyde group.
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Section 18.8
Q11 Exercise
Classify each of the following monosaccharides

according to both the number of carbon atoms and
the type of carbonyl group present.
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Section 18.8
Exercise
Classify each of the following monosaccharides

according to both the number of carbon atoms and
the type of carbonyl group present.
a. Aldopentose
b. Ketohexose
c. Aldohexose
d. Ketopentose
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Section 18.9
Biochemically Important Monosaccharides
D-Glucose
• Most abundant in nature

• Most important source of human nutrition
• Grape fruit and ripe fruits are good sources of
glucose (20–30% by mass)
– Also named grape sugar
• Other names
– Dextrose
– Blood sugar (70–100 mg/dL)
• Six-membered cyclic form
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Section 18.9
D-Galactose
• Milk sugar
• Synthesized in human beings
• Also called brain sugar
– Part of brain and nerve tissue
• Used to differentiate between blood
types
• Six-membered cyclic form
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Section 18.9
D-Fructose
• Ketohexose
• Sweetest tasting of all sugars
– Found in many fruits and in honey
• Good dietary sugar due to
higher sweetness
• Five-membered cyclic form
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Section 18.9
D-Ribose
• Part of a variety of complex molecules which

include:
– RNA
– ATP
– DNA
• Five-membered cyclic form
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Section 18.9
Monosaccharides
• The hexose monosaccharides are the
most important carbohydrate sources of
cellular energy.
• Three hexoses – glucose, galactose,
and fructose – are of major significance
in nutrition.
– All three have the same formula, C6H12O6,
and thus deliver the same amount of
cellular energy.
– They differ in structure, but are biologically
interconvertible.
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Section 18.9
• Glucose (dextrose)
– is the most important of the monosaccharides.
– an aldohexose and is found in the free state in plant and
animal tissue.
CHO
H OH
HO H
H OH
H OH
60
CH2OH Return to TOC
Section 18.9
Glucose
• Dextrose or grape sugar
• Found in bloodstream and tissue fluids
• Blood sugar
• Requires no digestion
• 80-100mg per mL of blood
61
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Section 18.9
Glucose®
• Diabetes Mellitus – high amount of

glucose in the blood
• Glycosuria – presence of glucose in urine
• Emotional Glycosuria – glucose in urine
during extreme excitement
• Alimentary Glucosuria – glucose in urine
after ingestion of large amounts of sugar.
62
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Section 18.9
Galactose
- is also an aldohexose and occurs, along
with glucose, in lactose and in many oligo-
and polysaccharides such as pectin and
gums. CHO CHO
H OH H OH
HO H HO H
H OH
HO H
H OH
H OH
C H 2O H
C H 2O H
Glucose
Galactose
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63
Section 18.9
Galactose
CHO CH2OH
CH2OH
H OH
OH OH O OH
O
HO H 
OH OH
HO H

H OH HO
CH2OH OH HO
D-galactose -D-galactopyranose -D-galactopyranose
64
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Section 18.9
Galactose
• D-galactose can be converted into D-glucose in the liver
by a specific enzyme “epimerase”.®
65
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Section 18.9
Galactose
• Galactosemia®
– Severe inherited disease
– Results in the inability of infants to metabolize
galactose due to lack of enzyme:
• galactose 1-phosphate uridyl transferase
• galactokinase
66
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Section 18.9
Galactose
• Galactosuria®
– Increase of galactose concentration in urine or blood
67
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Section 18.9
• Fructose
– also known as levulose, is a ketohexose that
occurs in fruit juices, honey, and along with
glucose, as a constituent of sucrose.
CH2OH
HO H
H OH
H OH
CH2OH 68
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Section 18.9
Fructose
C H 2O H
O
C H 2O H OH
HO H O 
H OH OH
H OH
C H 2O H
C H 2O H
OH
D-fructose β-D-fructose
69
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Section 18.9
Fructose
• Most soluble sugar®
• Sweetest of all sugars(75% sweeter than glucose)
• Invertase (in bees)- splits sucrose into glucose and
fructose.
• Metabolized directly
• Readily converted to glucose in the liver.
• Inulin - polysaccharide that contains fructose
– present in:
• dahlia tubers
• Chicory roots
• Jerusalem artichokes
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Section 18.9
Which monosaccharide is the most important from

a human nutritional standpoint?
a.D-Galactose
b.D-Mannose
c.D-Glucose
d.D-Fructose
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Section 18.9
Which monosaccharide is the most important from

a human nutritional standpoint?
a.D-Galactose
b.D-Mannose
c.D-Glucose
d.D-Fructose
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Section 18.10
Cyclic Forms of Monosaccharides
Cyclic Hemiacetal Forms of D-Glucose
• Dominant forms of monosaccharides with 5 or

more C atoms
– Cyclic structures are in equilibrium with open chain
forms
• Cyclic structures are formed by the reaction of
carbonyl group (C=O) with hydroxyl (–OH) group
on carbon 5
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Section 18.10
• Hemiacetal
– Has both an alcohol and an ether attached
to the aldehyde carbon.
• Acetal
– Has two ether groups attached to the
aldehyde carbon.
• Cyclic Hemiacetal or Cyclic Hemiketal
– If the alcohol and carbonyl groups are
within the same molecule.
– Intramolecular cyclization
74
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Section 18.10
Figure 18.17 - The Cyclic Hemiacetal Forms of D-
Glucose
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Section 18.10
Cyclic Hemiacetal Forms of D-Glucose
• 2 forms of D-Glucose:
– α-form where the –OH of C1 and CH2OH of C5 are
on opposite sides
– β-form where the –OH of C1 and CH2OH of C5 are
on the same side
6 6
CH2 OH Anomeric CH 2OH
O Carbon O OH
5 5
4 1 4
OH OH
1
2 OH 2
OH OH
3 3 Anomeric
OH OH Carbon
-D-Glucose -D-Glucose
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Section 18.10
Anomers
• Cyclic monosaccharides that differ only in the

position of the substituents on the anomeric
carbon atom
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Section 18.10
Cyclic Forms of Other Monosaccharides
• Intramolecular cyclic hemiacetal formation and

the equilibrium between various forms are not
restricted to glucose
• All aldoses with five or more carbon atoms
establish similar equilibria, but with different
percentages of the alpha, beta, and open-chain
forms
• Fructose and other ketoses with a sufficient
number of carbon atoms also cyclize
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Section 18.10
Pyranose and Furanose
• Pyranose - Cyclic monosaccharide containing a

six-atom ring
• Furanose - Cyclic monosaccharide containing a
five-atom ring
• Their ring structures resemble the ring structures
in the cyclic ethers pyran and furan, respectively
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Section 18.10
Monosaccharides in nature have cyclic forms

because they can form:
a.internal acetals that are stable.

b.internal hemiacetals that are stable.
c.internal acetals that are rapidly converted to stable
hemiacetals.
d.internal hemiacetals that are rapidly converted to stable
acetals.
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Section 18.10
Monosaccharides in nature have cyclic forms

because they can form:
a.internal acetals that are stable.

b.internal hemiacetals that are stable.
c.internal acetals that are rapidly converted to stable
hemiacetals.
d.internal hemiacetals that are rapidly converted to stable
acetals.
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Section 18.11
Haworth Projection Formulas
• Haworth projection formula: Two-dimensional

structural notation that specifies the three-
dimensional structure of a cyclic form of a
monosaccharide
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Section 18.11
α and β Configuration
• Determined by the position of the –OH group on C1
relative to the –CH2OH group that determines D or L
series
– In a β configuration, both of these groups point in the same
direction
– In an α configuration, the two groups point in opposite directions
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Section 18.11
–OH Group Position
• The specific identity of a monosaccharide is determined by the
positioning of the other –OH groups in the Haworth projection
formula
– Any –OH group at a chiral center that is to the right in a Fischer
projection formula points down in the Haworth projection formula
– Any –OH group to the left in a Fischer projection formula points
up in the Haworth projection formula
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Section 18.11
Haworth projection formula for a monosaccharide

is a formula showing:
a.a line structure of a stable internal acetal.

b.a two-dimensional notation that specifies the three-
dimensional structure of a cyclic monosaccharide.
c.a line structure of a stable internal hemiacetal.
d.a two-dimensional notation that specifies the three-
dimensional structure of a stable cyclic acetal.
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Section 18.11
Haworth projection formula for a monosaccharide

is a formula showing:
a.a line structure of a stable internal acetal.

b.a two-dimensional notation that specifies the three-
dimensional structure of a cyclic monosaccharide.
c.a line structure of a stable internal hemiacetal.
d.a two-dimensional notation that specifies the three-
dimensional structure of a stable cyclic acetal.
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Section 18.11
Which of the monosaccharides glucose, fructose,

galactose, and ribose has each of the following
structural characteristics? (There may be more than
one correct answer for a given characteristic)
a. It is a pentose.
b. It is a ketose.
c. Its cyclic form has a 6-membered ring.
d. Its cyclic form has two carbon atoms outside the ring.
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Section 18.11
Practice Exercise
Which of the monosaccharides glucose, fructose,

galactose, and ribose has each of the following
structural characteristics? (There may be more than
one correct answer for a given characteristic)
a. It is a pentose. Ribose
b. It is a ketose. Fructose
c. Its cyclic form has a 6-membered ring. Glucose, galactose
d. Its cyclic form has two carbon atoms outside the ring.
Fructose
Return to TOC

Section 18.12
Reactions of Monosaccharides
• Five important reactions of monosaccharides:

– Oxidation to acidic sugars
– Reduction to sugar alcohols
– Glycoside formation
– Phosphate ester formation
– Amino sugar formation
• Glucose will be used as the monosaccharide
reactant
• Other aldoses, as well as ketoses, undergo
similar reactions
Return to TOC

Section 18.12
Oxidation-Reduction
Return to TOC
Section 18.12
Oxidation-reduction (redox) is a
chemical process in which the
oxidation number of an element is
changed.
Return to TOC
Section 18.12
Redox may involve the complete

transfer of electrons to form ionic
bonds or a partial transfer of
electrons to form covalent bonds.
Return to TOC
Section 18.12
• Oxidation occurs when the oxidation number of an

element increases as a result of losing electrons.
• Reduction occurs when the oxidation number of an element

decreases as a result of gaining electrons.
• In a redox reaction oxidation and reduction occur
simultaneously, one cannot occur in the absence of the other.
Return to TOC
Section 18.12
• Oxidation Reduction
• 1. An increase in oxidation 1. A decrease in oxidation
• number number
• 2. A loss of electrons 2. A gain of electrons
• 3. A gain of oxygen 3. A loss of oxygen
• 4. A loss of hydrogen 4. A gain of hydrogen
Return to TOC
Section 18.12
• Oxidizing agent The substance that causes an

increase in the oxidation state of another substance.
– The oxidizing agent is reduced in a redox reaction.
• Reducing agent The substance that causes a decrease in

the oxidation state of another substance.
– The reducing agent is oxidized in a redox reaction.
Return to TOC
Section 18.12
Reactions of Aldehydes & Ketones
• Oxidation
– aldehydes only
• Reduction
– aldehydes and ketones
• Addition
– aldehydes and ketones
96
Return to TOC
Section 18.12
Oxidation of Aldehydes
• Aldehydes are easily oxidized to carboxylic acids by a

variety of oxidizing agents, including (under some
conditions) oxygen of the air.
O O
3 3
C + Cr2O72- + 8 H+ C + 3 Cr3+ + 4H2O
R H R OH
97
Return to TOC
Section 18.12
Oxidation of Ketones
• Ketones can be oxidized under drastic conditions
– treatment with hot potassium permanganate solution.
– carbon-carbon bonds are broken and variety of
products are formed.
98
Return to TOC
Section 18.12
Tollens test
• The Tollens test (silver-mirror test) for aldehydes is based

on the ability of silver ions to oxidize aldehydes.
O O
C + 2 Ag+ NH3 + 2 Ag (s)

C
H2O
R H R O-NH4+
99
Return to TOC
Section 18.12
• Tollen’s Reagent
– Solution of silver nitrate and ammonia in water
100
Return to TOC
Section 18.12
Fehling and Benedict Tests

• Fehling and Benedict solutions contain Cu2+ ions in an
alkaline medium.
• In these tests, the aldehyde group is oxidized to an acid by
Cu2+ ions.
O O
C + 2 Cu+2 NaOH C + 2 Cu2O (s)

H2O
R H blue R O-Na+ brick red
101
Return to TOC
Section 18.12
Tollens, Fehling & Benedict Tests
• Ketones do not give a positive with Tollens, Fehling, or

Benedict solutions. These tests are used to distinguish between
aldehydes and ketones.
C + 2 Cu+2 NaOH no reaction

H2O
R R
C + 2 Ag+ NH3
no reaction
H2O 102
R R Return to TOC
Section 18.12
Oxidation to Produce Acidic Sugars
• The redox chemistry of monosaccharides is

closely linked to the alcohol and aldehyde
functional groups
• Oxidation can yield three different types of acidic
sugars depending on the type of oxidizing agent
used
– Aldonic acid - Formed when weak oxidizing agents
such as Tollens and Benedict’s solutions oxidize the
aldehyde end
– Reducing sugar: Carbohydrate that gives a positive
test with Tollens and Benedict’s solutions Return to TOC

Section 18.12
Oxidation to Produce Acidic Sugars
• Strong oxidizing agents can oxidize both ends of

a monosaccharide at the same time (the
carbonyl group and the terminal primary alcohol
group) to produce a dicarboxylic acid
– Such polyhydroxy dicarboxylic acids are known as
aldaric acids
• In biochemical systems, enzymes can oxidize
the primary alcohol end of an aldose such as
glucose, without oxidation of the aldehyde
group, to produce an alduronic acid
Return to TOC

Section 18.12
Reduction to Produce Sugar Alcohols
• The carbonyl group in a monosaccharide (either

an aldose or a ketose) is reduced to a hydroxyl
group using hydrogen as the reducing agent
– The product is the corresponding polyhydroxy alcohol
called sugar alcohol or alditol
– Sorbitol - Used as a moisturizing agent in foods and
cosmetics and as a sweetening agent in chewing
gum
Return to TOC

Section 18.12
• Acetal
– Has two ether groups attached to the
aldehyde carbon.
106
Return to TOC
Section 18.12
Figure 18.17 - The Cyclic Hemiacetal Forms of D-
Glucose
Return to TOC

Section 18.12
Addition of Alcohols
• In the presence of excess alcohol and strong acid such as dry HCl,
aldehydes or hemiacetals react with a second molecule of the
alcohol to give an acetal:
OH OCH3
dry HCl
HC CH2CH3 + CH3OH HC CH2CH3 +H2O
OCH3 OCH3
1,1-dimethoxypropane
(propionaldehyde dimethyl acetal)
108
Return to TOC
Section 18.12
Acetals
• - compounds that have two alkoxy

groups on the same carbon atom (from
hemiacetal).
OH OCH3
dry HCl
HC CH2CH3 + CH3OH HC CH2CH3 +H2O
OCH3 OCH3
1,1-dimethoxypropane
(propionaldehyde dimethyl acetal)
Return to TOC
Section 18.12
• Cyclic structures of monosaccharides are intramolecular
hemiacetals.
• Five- or six-membered rings are especially stable.
CH2OH
hemiacetal structure
O in -D-glucopyranose
OH
HO HO
HO
110
Return to TOC
Section 18.12
Glycoside
• When a monosaccharide hemiacetal reacts with
an alcohol, the product is an acetal.
• In carbohydrate terminology, this acetal structure
is called a glycoside. CH OH
2
acetal structure
O
OH
HO RO
glycosidic linkage
HO
111
Return to TOC
Section 18.12
Glycosidic Linkages
C H 2O H C H 2O H
O O
HO OH
OH O HO
OH HO
 - 1 ,4 - g l y c o s i d i c l i n k a g e
Maltose
112
Return to TOC
Section 18.12
• Glycoside
– From Greek word “ glyks” = sweet
– Do not form open-chain compounds in aqueous
solutions
Return to TOC
Section 18.12
• Acetals tend to be more stable and less

reactive than hemiacetals
• Examples of Glycosides:
– Heart glycosides
• digitalis
• quabain
– Antibiotics
• streptomycin
• erythromycin
114
Return to TOC
Section 18.12
Glycloside Formation
• Glycoside: Acetal formed from a cyclic

monosaccharide by replacement of the
hemiacetal carbon –OH group with an –OR
group
– Glucoside - Glycoside produced from glucose
– Galactoside - Glycoside produced from galactose
– Exist in both α and β forms
Return to TOC

Section 18.12
Phosphate Ester Formation
• Hydroxyl groups of a monosaccharide can react

with inorganic oxyacids to form inorganic esters
• Phosphate esters of various monosaccharides
are stable in aqueous solution and play
important roles in the metabolism of
carbohydrates
Return to TOC

Section 18.12
Amino Sugar Formation
• Amino sugar - Formed when one of the hydroxyl

groups of a monosaccharide is replaced with an
amino group
• In naturally occurring amino sugars, the C2
hydroxyl group is replaced by an amino group
• Amino sugars and their N-acetyl derivatives are
important building blocks of polysaccharides
such as chitin and hyaluronic acid
Return to TOC

Section 18.12
Which of the following sugars cannot be oxidized

by Tollens and Benedict’s reagents in basic
conditions?
a.D-glucose, an aldohexose
b.D-fructose, a ketohexose
c.D-mannose, an aldohexose
d.sucrose
Return to TOC

Section 18.12
Which of the following sugars cannot be oxidized

by Tollens and Benedict’s reagents in basic
conditions?
a.D-glucose, an aldohexose
b.D-fructose, a ketohexose
c.D-mannose, an aldohexose
d.Sucrose
Return to TOC

Section 18.13
Disaccharides
• Two monosaccharides can react to form a

disaccharide
– One monosaccharide acts as a hemiacetal and the
other as an alcohol
– Resulting ether bond is a glycosidic linkage
Return to TOC

Section 18.13
Disaccharides
Maltose (Malt Sugar)

• Structurally made of 2 D-glucose units, one of
which must be α-D-glucose, linked via an
α(14) glycosidic linkage
• Digested easily by humans because of an
enzyme that can break α(14) linkages
• Baby foods are rich in maltose
Return to TOC

Section 18.13
Disaccharides
Cellobiose
• Produced as an intermediate in the hydrolysis of

the polysaccharide cellulose
– Contains two D-glucose monosaccharide units, one
of which must have a β configuration, linked
through a β(14) glycosidic linkage
• Cannot be digested by humans
Return to TOC

Section 18.13
Disaccharides
Lactose
• Made up of β-D-galactose unit and a D-
glucose unit joined by a β(14) glycosidic
linkage
• Milk is rich in the disaccharide lactose
• Lactase hydrolyzes β(14) glycosidic linkages
Return to TOC

Section 18.13
Disaccharides
Lactose Intolerance or Lactase Persistence
• Lactose is the principal carbohydrate in milk

– Human mother’s milk - 7%–8% lactose
– Cow’s milk - 4%–5% lactose
• Lactose intolerance is a condition in which
people lack the enzyme lactase needed to
hydrolyze lactose to galactose and glucose
• Deficiency of lactase can be caused by a
genetic defect, physiological decline with age, or
by injuries to intestinal mucosa
Return to TOC

Section 18.13
Disaccharides
Lactose Intolerance or Lactase Persistence
• When lactose is undigested, it attracts water

causing fullness, discomfort, cramping, nausea,
and diarrhea
• Bacterial fermentation of the lactose further
along the intestinal tract produces acid (lactic
acid) and gas, adding to the discomfort
Return to TOC

Section 18.13
Disaccharides
Sucrose (Table Sugar)
• The most abundant of all disaccharides and
found in plants
• Produced commercially from the juice of sugar
cane and sugar beets
– Sugar cane contains up to 20% by mass sucrose
– Sugar beets contain up to 17% by mass sucrose
Return to TOC

Section 18.13
Disaccharides
Disaccharides
• Disaccharides are carbohydrates composed of two
monosaccharide residues united by a glycosidic
linkage.
H+ or sucrase
• sucrose + water  glucose + fructose
 galactose + glucose
H+ or
• lactose + water lactase
• maltose + water  H+glucose

or
+ glucose
maltase
127
Return to TOC
Section 18.13
Disaccharides
Return to TOC

Section 18.13
Disaccharides
What is the linkage that is formed when two

monosaccharides react to form a disaccharide
called?
a.Alcohol group linkage

b.Glycosidic linkage
c.Hemiacetal linkage
d.Acetal linkage
Return to TOC

Section 18.13
Disaccharides
What is the linkage that is formed when two

monosaccharides react to form a disaccharide
called?
a.Alcohol group linkage

b.Glycosidic linkage
c.Hemiacetal linkage
d.Acetal linkage
Return to TOC

Section 18.13
Disaccharides
Which disaccharide is a nonreducing sugar?
a.Maltose
b.Lactose
c.Cellobiose
d.Sucrose
Return to TOC

Section 18.13
Disaccharides
Which disaccharide is a nonreducing sugar?
a.Maltose
b.Lactose
c.Cellobiose
d.Sucrose
Return to TOC

Section 18.13
Disaccharides

Which of these disaccharides, i.e., maltose, cellobiose,
lactose, and sucrose, have the following structural or
reaction characteristics? (There may be more than one
correct answer for a given characteristic)
a.Two different monosaccharide units are present.
b.Hydrolysis produces only monosaccharides.
c.Its glycosidic linkage is a “head-to-head” linkage.
d.It is not a reducing sugar.

Return to TOC

Section 18.13
Disaccharides
Practice Exercise
Which of these disaccharides, i.e., maltose, cellobiose,
lactose, and sucrose, have the following structural or
reaction characteristics? (There may be more than one
correct answer for a given characteristic)
a.Two different monosaccharide units are present.
Lactose, sucrose
b.Hydrolysis produces only monosaccharides.
Maltose, cellobiose, lactose, sucrose
c.Its glycosidic linkage is a “head-to-head” linkage.
Sucrose
d.It is not a reducing sugar.
Sucrose Return to TOC

Section 18.14
Oligosaccharides
• Carbohydrates that contain 3–10

monosaccharide units bonded to each other via
glycosidic linkages
• Generally present in association with other
complex molecules
– Raffinose - Made of 1 galactose, 1 glucose, and 1
fructose
– Stachyose - Made of 2 galactose, 1 glucose, and 1
fructose units
• Commonly found in onions, cabbage, broccoli,
and whole wheat
Return to TOC

Section 18.14
Oligosaccharides
Blood Types and Oligosaccharides
• Human blood is classified into four types

– A, B, AB, and O
– The basis for the difference is the type of sugars
(oligosaccharides) present
– Blood of one type cannot be given to a recipient with
blood of another type
– A transfusion of wrong blood type can cause the
blood cells to form clumps, a potentially fatal reaction
– People with type O blood are universal donors, and
those with type AB blood are universal recipients
Return to TOC

Section 18.14
Oligosaccharides
Blood Types and Oligosaccharides
• In the United States, type O blood is the most

common and type A the second most common
• The biochemical basis for the various blood
types involves oligosaccharides present on
plasma membranes of red blood cells
• The oligosaccharides responsible for blood
groups are D-galactose and its derivatives
Return to TOC

Section 18.14
Oligosaccharides
Other Oligosaccharides
• Solanine, a potato plant toxin, is a

oligosaccharide found in association with an
alkaloid
– Bitter taste of potatoes is due to relatively higher
levels of solanine
Return to TOC

Section 18.14
Oligosaccharides
Which of the following is a toxin produced by

potato plants?
a.Raffinose
b.Stachyose
c.Solanine
d.None of the above
Return to TOC

Section 18.14
Oligosaccharides
Which of the following is a toxin produced by

potato plants?
a.Raffinose
b.Stachyose
c.Solanine
d.None of the above
Return to TOC

Section 18.15
General Characteristics of Polysaccharides
The Polymer Chain
• Polysaccharides are polymers of many

monosaccharide units bonded with glycosidic
linkages
• Two types:
– Homopolysaccharide
– Heteropolysaccharide
Return to TOC

Section 18.15
Figure 18.26 - The Polymer Chains of a Polysaccharide
Return to TOC

Section 18.15
Characteristics of Polysaccharides
• Polysaccharides are not sweet and do not show

positive tests with Tollen’s and Benedict’s
solutions, whereas monosaccharides are sweet
and show positive tests
• Limited water solubility
• Examples:
– Cellulose and glycogen - Storage polysaccharides
– Chitin - Structural polysaccharide
– Hyaluronic acid - Acidic polysaccharide
Return to TOC

Section 18.15
A _____ is a polysaccharide in which only one

type of monosaccharide monomer is present.
a.heteropolysaccharide
b.homopolysaccharide
c.heteromonosaccharide
d.homomonosaccharide
Return to TOC

Section 18.15
A _____ is a polysaccharide in which only one

type of monosaccharide monomer is present.
a.heteropolysaccharide
b.homopolysaccharide
c.heteromonosaccharide
d.homomonosaccharide
Return to TOC

Section 18.16
Storage Polysaccharides
Starch
• Storage polysaccharide: Polysaccharide that is

a storage form for monosaccharides and used
as an energy source in cells
• Starch
– Glucose is the monomeric unit
– Storage polysaccharide in plants
Return to TOC

Section 18.16
Types of Polysaccharides Isolated From Starch
• Amylose
– Unbranched-chain polymer and accounts for 15%–
20% of the starch
– Has α(14) glycosidic bonds
• Amylopectin
– Branched chain polymer and accounts for 80%–85%
of the starch
– Has α(14) and α(16) glycosidic bonds
– Up to 100,000 glucose units are present
– Amylopectin is digested more readily by humans
(can hydrolyze α linkages but not β linkages) Return to TOC

Section 18.16
Glycogen
• Glucose storage polysaccharide in humans and

animals
• Contains only glucose units
• Branched chain polymer with α(14) glycosidic
bonds in straight chains and α(16) in
branches
• Three times more highly branched than
amylopectin in starch
• Contains up to 1,000,000 glucose units
Return to TOC

Section 18.16
Glycogen
• Excess glucose in blood is stored in the form of

glycogen
Glycogenesis
Glucose Glycogenolysis
glycogen
Return to TOC

Section 18.16
In starch, two different glucose-containing

polysaccharides can be isolated. They are _____
and _____.
a.glycogen; amylose
b.amylose; amylopectin
c.amylose; cellulose
d.glycogen; cellulose
Return to TOC

Section 18.16
In starch, two different glucose-containing

polysaccharides can be isolated. They are _____
and _____.
a.glycogen; amylose
b.amylose; amylopectin
c.amylose; cellulose
d.glycogen; cellulose
Return to TOC

Section 18.17
Structural Polysaccharides
Cellulose
• Linear homopolysaccharide with β(14)

glycosidic bond
• Contains up to 5000 glucose units with
molecular mass of 900,000 amu
– Cotton has 95% cellulose and wood 50% cellulose
• Humans do not have enzymes that hydrolyze
β(14) linkages and so they cannot digest
cellulose
– Animals also lack these enzymes, but they can
digest cellulose due to the presence of cellulase-
producing bacteria Return to TOC

Section 18.17
Cellulose
• It serves as dietary fiber in food and readily

absorbs water resulting in softer stools
– 20–35 g of dietary fiber is desired everyday
Return to TOC

Section 18.17
Chitin
• Similar to cellulose structurally and functionally

• Linear polymer with all β(14) glycosidic
linkages
– It has an N-acetyl amino derivative of glucose
• Function is to give rigidity to the exoskeletons of
crabs, lobsters, shrimp, insects, and other
arthropods
Return to TOC

Section 18.17
Figure 18.32(b) - The Structure of Chitin
Return to TOC

Section 18.17
What is the structural component of plant cell

walls?
a.Starch
b.Glycogen
c.Chitin
d.Cellulose
Return to TOC

Section 18.17
What is the structural component of plant cell

walls?
a.Starch
b.Glycogen
c.Chitin
d.Cellulose
Return to TOC

Section 18.18
Acidic Polysaccharides
Acidic polysaccharides
• Polysaccharides with a repeating disaccharide

unit containing an amino sugar and a sugar with
a negative charge due to a sulfate or a carboxyl
group
• They are heteropolysaccharides, i.e., different
monosaccharides exist in an altering pattern
• Examples:
– Hyaluronic acid
– Heparin
Return to TOC

Section 18.18
Hyaluronic Acid
• Alternating residues of N-acetyl- β-D-

glucosamine and D-glucuronate
• Highly viscous and serve as lubricants in the
fluid of joints as well as vitreous humor of the
eye
Return to TOC

Section 18.18
Heparin
• Polysaccharide with 15–90 disaccharide

residues per chain
• Blood anticoagulant
Return to TOC

Section 18.18
Heparin, a well known acidic polysaccharide, is

best known for its biochemical function as a(n)
_____.
a.coagulant
b.anticoagulant
c.exoskeleton
d.dietary fiber
Return to TOC

Section 18.18
Heparin, a well known acidic polysaccharide, is

best known for its biochemical function as a(n)
_____.
a.coagulant
b.anticoagulant
c.exoskeleton
d.dietary fiber
Return to TOC

Section 18.19
Dietary Considerations and Carbohydrates
Nutrition
• Foods high in carbohydrate content constitute

over 50% of the diet of most people of the world
– Corn in South America
– Rice in Asia
– Starchy root vegetables in parts of Africa
– Potato and wheat in North America
• Balanced dietary food should contain about 60%
of carbohydrate
Return to TOC

Section 18.19
Classes of Dietary Carbohydrates
• Simple carbohydrates: Dietary

monosaccharides or disaccharides
– Sweet to taste and commonly referred to as sugars
– Constitute 20% of the energy in the US diet
• Complex carbohydrates: Dietary
polysaccharides
– Include starch and cellulose, which are normally not
sweet to taste
Return to TOC

Section 18.19
Dietary carbohydrates constitute _____ of the diet

of most people.
a.10%
b.25%
c.35%
d.50%
Return to TOC

Section 18.19
Dietary carbohydrates constitute _____ of the diet

of most people.
a.10%
b.25%
c.35%
d.50%
Return to TOC

Section 18.20
Glycolipids and Glycoproteins: Cell Recognition
• Glycolipid: Lipid molecule that has one or more

carbohydrate (or carbohydrate derivative) units
covalently bonded to it
• Glycoprotein: Protein molecule that has one or
more carbohydrate (or carbohydrate derivative)
units covalently bonded to it
– Such carbohydrate complexes are very important in
cellular functions such as cell recognition
Return to TOC

Section 18.20
A protein molecule that has one or more

carbohydrate units covalently bonded to it is
known as a(n) _____.
a.glycolipid
b.glucoprotein
c.glycoprotein
d.oligosaccharide protein
Return to TOC

Section 18.20
A protein molecule that has one or more

carbohydrate units covalently bonded to it is
known as a(n) _____.
a.glycolipid
b.glucoprotein
CT1
c.glycoprotein
d.oligosaccharide protein
Return to TOC

Slide 169
CT1 no such thing as glucoprotein

Cynthia Talens, 7 Sep 2021
Chapter 18
The End!
Thank you for listening.
Return to TOC

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Section 18.

Copyright ©2016 Cengage Learning. All Rights Reserved. 1

Copyright ©2016 Cengage Learning. All Rights Reserved. 2

The Study of Living Things

• Biochemistry: Study of the chemical

Copyright ©2016 Cengage Learning. All Rights Reserved. 3

Bioinorganic and Bioorganic Substances

• As isolated compounds, bioinorganic and

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a.carbohydrates, lipids, proteins, and salts.

Copyright ©2016 Cengage Learning. All Rights Reserved. 5

Biochemistry, the study of the chemical

a.carbohydrates, lipids, proteins, and salts.

Copyright ©2016 Cengage Learning. All Rights Reserved. 6

Plants and Carbohydrates

• It is estimated that more than half of all organic

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• Most of the matter in plants, except water, is

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• Process in which plants produce carbohydrates

CO 2 + H 2 O + solar energy 

Copyright ©2016 Cengage Learning. All Rights Reserved. 9

Functions of Carbohydrates in the Human Body

• Carbohydrate oxidation provides energy

Copyright ©2016 Cengage Learning. All Rights Reserved. 10

Functions of Carbohydrates in the Human Body

• Carbohydrates linked to lipids are structural

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a.They provide energy during their oxidation and a short-term

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Identify the functions of carbohydrates in the

a.They provide energy during their oxidation and a short-term

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• Empirical formula of simple carbohydrates -

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• Contain single polyhydroxy aldehyde or ketone

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• Contain 2 monosaccharide units covalently

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• Contain three to ten monosaccharide units

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• Contain many monosaccharide units covalently

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Carbohydrates are classified as:

a.monosaccharides, disaccharides, oligosaccharides, and

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Carbohydrates are classified as:

a.monosaccharides, disaccharides, oligosaccharides, and

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Objects and Handedness

• Most biological molecules, including

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• Mirror image: Reflection of an object in a mirror

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Indicate whether the circled carbon atom in each

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Indicate whether the circled carbon atom in each

a. Not a chiral center b. Not a chiral center

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A carbohydrate molecule whose mirror image is

Copyright ©2016 Cengage Learning. All Rights Reserved. 27