BIOCHEMISTRY

Carbohydrates
Chapter 18
Table of Contents
18.1Biochemistry—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 Projections 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 General Characteristics of Polysaccharides
18.15 Storage Polysaccharides
18.16 Structural Polysaccharides
18.17 Acidic Polysaccharides
18.18 Glycolipids and Glycoproteins: Cell Recognition
18.19 Dietary Considerations and Carbohydrates
Copyright © Cengage Learning. All rights reserved 2

Section 18.1
Biochemistry – An Overview
The Study of Living Things

• Biochemistry is the study of the chemical substances
found in living organisms and the chemical interactions
of these substances with each other.
• A biochemical substance is a chemical substance found
within a living organism.
• Two types of biochemical substances: bioinorganic
substances and bioorganic substances.
– Bioinorganic substances : water and inorganic
salts.
– Bioorganic substances : carbohydrates, lipids,
proteins, and nucleic acids
Return to TOC

Section 18.1
The Study of Living Things

• As isolated compounds, bioinorganic and bioorganic
substances have no life in and of themselves. Yet when
these substances are gathered together in a cell, their
chemical interactions are able to sustain life.
• 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.
Return to TOC

Section 18.1
Figure 18.1: Biochemical Substances, Mass

Composition Data fo the Human Body
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Section 18.2
Occurrence and Functions of Carbohydrates
Photosynthesis
• 75% of dry plant material: Produced by photosynthesis
• Cellulose: structural element
• Starch/glycogen: energy reservoir
- small amount in human body
• Plant products are source of carbohydrates
- average human diet contains 2 /3 of carbohydrates
Most of the matter in plants, except water, is carbohydrate
material.
Return to TOC

Section 18.2
Figure 18.2 : Most of the matter in plants,
except water, is carbohydrate
© PictureNew/Corbis
Return to TOC
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
• Carbohydrates linked to lipids (Chapter 19) are structural
components of cell membranes
• Carbohydrates linked to proteins (Chapter 20) function in a
variety of cell–cell and cell–molecule recognition processes
Return to TOC

Section 18.3
Classification of Carbohydrates
Photosynthesis
• Simpler Formula:
– CnH2nOn or Cn(H2O)n (hydrates of C)
– n= number of atoms
• Carbohydrates are polyhydroxy aldehydes or ketones or
compounds that produce such substances upon
hydrolysis
CHO CH2 OH
Aldehyde H OH O Ketone
HO H HO H
H OH H OH
H OH H OH
Polyhydroxy
CH2 OH CH2 OH
Polyhydroxy ketone
aldehyde Glucose Fructose
Return to TOC

Section 18.3
Monosaccharide
• Contain single polyhydroxy aldehyde or ketone unit
• They can’t be broken down into simpler substances by
hydrolysis (reaction with water) reactions
• Contains 3 -7 C atoms
• 5 and 6 carbon species are more common
• Water soluble white crystalline solids
CHO CH2 OH
H OH O
HO H HO H Glucose and
H OH H OH
H OH H OH
fructose are
CH2 OH CH2 OH monosaccharides
Glucose Fructose Return to TOC

Section 18.3
Oligosaccharides
• Contains ~2 -10 monosaccharide units - covalently
bonded to each other
• Disaccharides (contain 2 monosaccharide units) more
common - crystalline water soluble substances
• Table sugar (sucrose) and milk sugar (lactose)
- are common disaccharides
• Upon hydrolysis they produce monosaccharide
• In human body associated with proteins and lipids for
structural and regulatory functions
Return to TOC

Section 18.3
Polysaccharides
• Contains many monosaccharide units covalently bonded
• Polymers: May contain 100s of 1000s of
monosaccharide units
• Examples:
• Cellulose: Paper, cotton, wood
• Starch: Bread, pasta, potatoes, rice, corn, beans,
peas, etc.
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Section 18.3
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Section 18.3
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Section 18.4
Chirality: Handedness in Molecules
Objects and Mirror Images

• Most monosaccharides exist in two forms: a “left
handed” and “right handed” form - same as two hands
• Two types of objects:
- Superimposable on their mirror images: -- images
that coincide at all points when the images are laid
upon each other -- a dinner plate with no design
features -- Achiral
- Non-superimposable on their mirror images: Chiral
(handedness)
Return to TOC

Section 18.4
Figure 18.3 : The mirror Image of the right hand is the left
hand. Hands (superimposable on their mirror images)
The property of handedness is not restricted to carbohydrates. It is a

general phenomenon found in all classes of organic compounds. Return to TOC
Section 18.4
Figure 18.4: A person’s right and left hands are
not superimposable upon each other
© Brooks/Cole, Cengage Learning. All rights reserved.
Return to TOC
Section 18.4
Chirality
• Chiral Center: C atom attached to 4 different groups bonded to it

• A molecule with chiral center is a chiral molecule
– Best way to visualize - look at all C atoms and see if there are
at least two H atoms then that can’t be a chiral center
– C atoms with less than one H atoms are worth looking at for
their chirality.
• An achiral molecule is a molecule whose mirror images are
superimposable.
• Achiral molecules do not posses handedness.
Return to TOC

Section 18.4
• Be careful as a C atom may apparently look similar but may not have
four DIFFERENT groups.
E. g. 3-bromopentane - C has two CH -CH groups – so it is achiral . A

2 3
chiral C is usually denoted by *
Br
*
3 -Bromopentane
Return to TOC

Section 18.4
Practice Exercise
Answers:
a. Not a chiral
center
b. Not a chiral
center Return to TOC
Copyright © Cengage Learning. All rights reserved c. Chiral center 20

Section 18.4
Responses of Left and Right Handed Forms of

a Molecule in a Human Body
– Both may be active, one may be more active or one

may be active and other non-active
– Example: Right handed hormone epinephrine is 20
times more active than left handed form
– Almost all monosaccharides are right handed
– Amino acids are almost always left handed
Return to TOC

Section 18.5
Stereoisomerism: Enantiomers and Diasterioisomers
Stereoisomers
• Stereoisomers are isomers that have the same
molecular and structural formulas but differ in the
orientation of atoms in space.
• Two types:
• Enantiomers are stereoisomers whose molecules are
nonsuperimposable mirror images of each other.
Molecules with chiral center.
• Diastereomers are stereoisomers whose molecules are
not mirror images of each other.
Return to TOC

Section 18.5
Figure 18.6: (a) Enantiomers and (b)

Diastereomers
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Section 18.5
Figure 18.7: Classifying Enantiomers and
Diastereomers
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Section 18.6
Designating Handedness Using Fischer Projection Formulas
Figure 18.8: The German

chemist Hermann Emil Fischer
(1852 -1919) developed the
two-dimensional system for
specifying chirality. He was
one of the early greats in
organic chemistry. In 1902 , he
was awarded the second
Nobel Prize in chemistry.
Edgar Fahs Smith Collection, University of Pennsylvania Library
Return to TOC
Section 18.6
Fischer Project Formulas

• Fischer projection formulas - a method for giving
molecular chirality specifications in two dimensions. A
Fischer projection formula is a two-dimensional structural
notation for showing the spatial arrangement of groups
about chiral centers in molecules.
• In a Fischer projection formula a chiral center (Carbon) is
represented as the intersection of vertical and horizontal
lines
• Functional groups of high priority will be written at top
• D and L system used to designate the handedness of
glyceraldehyde enantiomers
Return to TOC

Section 18.6
Tetrahedral Arrangements
• The four groups attached to the atom at the chiral center
assume a tetrahedral geometry and it is 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
Return to TOC

Section 18.6

• D and L system used to designate the handedness of
glyceraldehyde enantiomers (see figure below)
CHO CHO
H OH HO H
CH2OH CH2OH
D-Glyceroldehyde L-Glyceroldehyde
(-OH on right side) (-OH on left side)
Return to TOC

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—two
pairs of enantiomers
Return to TOC

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 are diastereomers whose molecules differ only
in the configuration at one chiral center
Return to TOC

Section 18.6
Exercise
Return to TOC

Section 18.7
Properties of Enantiomers
Constitutional Isomers and Diastereomers

• Constitutional isomers differ in most chemical and
physical properties. For example, constitutional isomers
have different boiling points and melting points.
• Diastereomers also differ in most chemical and physical
properties. They also 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: Move in all directions
– Plane polarized light move only in
one direction (see Figure on right
side)
• 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 enantiomer
• Same concentration of two enantiomers
rotate light to same extent but in opposite
direction
Return to TOC

Section 18.7
Dextrorotary and Levorotatory Compounds

• Enantiomers are optically active: Compounds that rotates the plane
polarized light
• Two Types:
– Dextrorotatory:
• Chiral compound that rotates light towards right (clockwise;
+)
– Levorotatory:
• Chiral compound that rotates light towards left
(counterclockwise; -)
– There is no correlation between D, L and +, -
• In D and L you need to look at the structure
• + and - are determined by using a polarimeter
Return to TOC

Section 18.7
Figure 18.10: Schematic Depiction of
Polarimeter
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Section 18.7
Interactions Between Chiral Compounds

• Right and Left handed baseball players can’t use same
glove (chiral) but can use same hat (achiral)
– Two members of 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
• Enantiomers have same boiling points, melting points
and densities - all these are dependent upon
intermolecular forces and chirality doesn’t depend on
them
Return to TOC

Section 18.7
Interactions Between Chiral Compounds

• Our body responds differently to different enantiomers:
• One may give higher rate or one may be inactive
– Example: Body response to D form of hormone
epinephrine is 20 times greater than its L isomer
Return to TOC

Section 18.7
Figure 18.11: The distincly different natural
flavors of Spearmint and Caraway are caused
by enantiomeric molecules,
Return to TOC
Section 18.7
Figure18.11: Spearmint leaves contain L-

carvone and caraway seeds contain D-carvone.
Return to TOC
Section 18.8
Classification of Monosaccharides
Monosaccharides
• Triose --- 3 carbon atoms
• Tetrose -- 4 carbon atoms
• Pentoses – 5 carbon atoms
• Hexoses -- 6 carbon atoms
• Aldoses: Monosaccharides with one aldehyde group
• Ketoses: Monosaccharides with one ketone group
• Combined # of C atoms and functional group:
– Example: Aldohexose: Monosaccharide with
aldehyde group and 6 C atoms
Return to TOC

Section 18.8
Most Common Monosaccharides
• Example: CHO CH2OH

– Aldohexose:
H OH O
Monosaccharide with
HO H HO H
aldehyde group and 6 C
atoms – D-glucose H OH H OH
– Ketohexose: H OH H OH
Monosaccharide with
CH2OH CH2OH
ketone group and 6 C
D-Glucose D-Fructose
atoms – D-fructose (aldohexose) (ketohexose)
Return to TOC

Section 18.8
Exercise
Return to TOC

Section 18.9
Biochemically Important Monosaccharides
Glucose and Fructose

CHO
H OH 1. Most abundant in nature

2. Nutritionally
HO H most important
3.H Grape OH fruit good source of glucose (20 - 30%
H
by mass)
OH
-- also named grape sugar, dextrose
and
CH2 OH
blood sugar (70 - 100 mg/100 mL of blood)
4.D-Glucose
Six membered cyclic form
(aldohexose)
CH2 OH
O 1. Ketohexose
HO H 2. Sweetest tasting of all sugars
H OH
3. Found in many fruits and in honey
H OH
4. Good dietary sugar-- due to higher sweetness
CH2 OH
5. Five membered cyclic form
D-Fructose
(ketohexose)
Return to TOC

Section 18.9
Figure 18.15: A 5% (m/v)

glucose solution is often
used in hospitals as
intravenous source of
nourishment for patients
who cannot take food by
mouth. The body can use it
as an energy source
without digesting it.
C. Paxton & J. Farrow/Photo Researchers
Return to TOC
Section 18.9
Galactose and Ribose

CHO
H OH
1. Milk sugar
HO H
2. Synthesize in human
HO H
3. Also called brain sugar-- part of brain and
H OH
CH2 OH
nerve tissue
4. Used to differentiate between blood types
DGalactose
5. Six membered cyclic form
(aldohexose)
CHO
H OH
H OH
H OH 1. Part of RNA
2. Part of ATP
CH2 OH 3. Part of DNA
4. Five membered cyclic form
DRibose
(aldopentose)
Return to TOC

Section 18.10
Cyclic Forms of Monosaccharides
Cyclic Hemiacetal Forms of D-Glucose
• Dominant form of
monosaccharides with 5 or
more C atoms is cyclic - cyclic
forms are in equilibrium with
open chain form
• Cyclic forms are formed by
the reaction of carbonyl group
(C=O) with hydroxyl (-OH)
group on carbon 5
Return to TOC

Section 18.10
Cyclic Hemiacetal Forms of D-Glucose

• 2 forms of D-glucose:
– Alpha-form: -OH of C1 and CH2OH of C5 are on opposite
sides
– Beta-form: -OH of C1 and CH2OH of C5 are on same
sides
6 6
CH2 OH CH 2 OH
O O OH
5 5
4 1 4
OH OH
1
2 OH 2
OH OH
3 3
OH OH
-D-Glucose -D-Glucose
Return to TOC

Section 18.10
• 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.
Return to TOC

Section 18.10
Pyranose and Furanose

• A cyclic monosaccharide containing a six-atom ring is
called a pyranose, and one containing a five-atom ring
is called furanose because their ring structures
resemble the ring structures in the cyclic ethers pyran
and furan respectively.
Pyran Furan
O
O
CH2 OH
CH2 OH CH2 OH
OH CH2 OH O
O
OH OH
OH
OH
-D-Glucose OH OH
OH OH
OH
 -D-Fructose  -D-Ribose
Pyranose Furanoses Return to TOC

Section 18.11
Haworth Projection Formulas
Figure 18.17: Walter

Norman Haworth
(1883 01950), the
developer of Haworth
projection formulas, was
a British carbohydrate
chemist. 193 7 corecipient
of the Nobel Peace Prize
in Chemistry.
© HultonDeutsch Collection/Corbis
Return to TOC
Section 18.11
• A Haworth projection formula is a two-dimensional

structural notation that specifies the three-dimensional
structure of a cyclic form of a monosaccharide.
CH2 OH
O CH2 OH
CH2 OH CH2 OH
O O
OH
OH
OH OH
OH OH
OH OH
OH OH
-D-Glucose  -D-Fructose  -D-Ribose
Return to TOC

Section 18.11
Alpha and Beta Configuration
• Alpha or Beta configuration is determined by the position

of the —OH group on C1 relative to the CH2OH group
that determines D or L series.
• In a Beta configuration, both of these groups point in
the same direction
• In an Alpha configuration, the two groups point in
opposite directions.
Return to TOC

Section 18.11
OH Group
• 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 and any —OH group to the left in a
Fischer projection formula points up in the Haworth
projection formula.
Return to TOC

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.
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.
Answers:
a. Ribose
b. Fructose
c. Glucose, galactose
Return to TOC
d. Fructose
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
• These reactions will be considered with respect to
glucose.
• Other aldoses, as well as ketoses, undergo similar
reactions.
Return to TOC

Section 18.12
Oxidation
• Oxidation to acidic sugars: The redox chemistry of
monosaccharides is closely linked to the alcohol
and aldehyde functional groups present in them.
• Oxidation can yield three different types of acidic
sugars depending on the type of oxidizing agent
used:
– Weak oxidizing agents such as Tollens and
Benedict’s solutions oxidize the aldehyde end to
give an aldonic acid.
– A reducing sugar is a carbohydrate that gives
a positive test with Tollens and Benedict’s
solutions.
Return to TOC

Section 18.12
Oxidizing Agents
• 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.
Return to TOC

Section 18.12
Oxidization
• 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
Figure 18.18: The

glucose to a color chart
that indicates glucose
concentration content of
urine can be determined
by dipping plastic strip
treated with oxidizing
agents into the urine
sample and comparing
the color change of the
strip
Return to TOC
Section 18.12
Sugar Alcohols
• Reduction to 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
- sugar alcohol.
– Sorbitol - used as moisturizing agents in foods and
cosmetics and as a sweetening agent in chewing
gum
Return to TOC

Section 18.12
Glycloside
• Glycoside formation: Cyclic forms of monosaccharides
are hemiacetals, they react with alcohols to form acetals:
– Monosaccharide acetals are called glycoside
• A glycoside is an acetal formed from a cyclic
monosaccharide by replacement of the hemiacetal
carbon —OH group with an —OR group:
– A glycoside produced from glucose - glucoside
– A glycoside produced from galactose – galactoside
– Glycosides exist in both Alpha and Beta forms
Return to TOC

Section 18.12
Blood Types and Monosaccharides

• Blood Types and Monosaccharides: Human blood is
classified into four types: A, B, AB, and O:
– 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 18.12
Blood Types
• 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 monosaccharides present on plasma
membranes of red blood cells.
• The monosaccharides responsible for blood groups
are D-galactose and its derivatives.
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Section 18.12
Differences Between Blood Types
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Section 18.12
Phosphate Ester Formation

• Phosphate ester formation: The 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 formation: An amino sugar - one of the
hydroxyl groups of a monosaccharide is replaced with an
amino group
• In naturally occurring amino sugars the carbon 2
hydroxyl group is replaced by an amino group
• Amino sugars and their N-acetyl derivatives are
important building blocks of polysaccharides such as
chitin
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Section 18.13
Disaccharides
• Two monosaccharides can react to form disaccharide

• One monosaccharide act as a hemiacetal and other as
alcohol
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Section 18.13
Disaccharides
Cellobiose
• Cellobiose is produced as an intermediate in the
hydrolysis of the polysaccharide cellulose:
– Cellobiose contains two β - D-glucose
monosaccharide units linked through a β (1—4)
glycosidic linkage.
CH2 OH
O OH
CH2 OH  (1-4)
H
O OH
O
OH
OH
OH
OH
Cellobiose
Return to TOC

Section 18.13
Disaccharides
Maltose
• Maltose is digested easily by humans because we have
enzymes that can break α (1-4) linkages but not β (1-4)
linkages of cellobiose. Therefore cellobiose cannot be
digested by humans.
CH2 OH CH2 OH
O O
OH OH
O OH
OH
 (14)
OH OH
Maltose
Return to TOC

Section 18.13
Disaccharides
Figure 18.19: Three Forms of Maltose
Return to TOC
Section 18.13
Disaccharides
Lactose
• Lactose is made up of β-D-galactose unit and a β-D-
glucose unit joined by a β(1-4) glycosidic linkage
CH2 OH
O OH
 (1-4)
CH2 OH H
OH
OH O O
OH
OH
OH
Lactose
Return to TOC

Section 18.13
Disaccharides
Lactose
• Lactose - principal carbohydrate in milk.
– Human - 7%–8% lactose
– cow’s milk - 4%–5% lactose
– Lactose intolerance: a condition in which people lack the
enzyme lactase needed to hydrolyze lactose to galactose and
glucose.
– Lactase hydrolyzes β(1-4) glycosidic linkages.
– Deficiency of lactase can be caused by a genetic defect,
physiological decline with age, or by injuries to intestinal
mucosa.
– 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
Human milk contains

more lactose than
does cow’s milk.
Lactose intolerance
is a condition I which
people lack the
enzyme lactase,
which is needed to
hydrolize lactose to
galactose and
glucose. © Erica Stone/Peter Arnold, Inc.
Return to TOC
Section 18.13
Disaccharides
Sucrose
• Sucrose (table sugar): The CH2 OH
most abundant of all O
disaccharides and found in OH

CH2 OH
plants.
O
OH OH
OH OH
• It is produced commercially -D-Glucose OH
from the juice of sugar cane + OH

O
 (1-2 )
Linkage
and sugar beets. CH2 OH
O OH
CH2 OH
O
– Sugar cane contains up OH OH
CH 2 OH CH 2 OH
to 20% by mass sucrose OH OH
– Sugar beets contain up -D-Fructose Sucrose
to 17% by mass sucrose
Return to TOC

Section 18.13
Disaccharides
Figure 18.2 1: Honeybees and

many other insects possess an
enzyme called invertase that
hydrolyzes sucrose to invert
sugar. Thus honey is
predominantly a mixture of D-
glucose and D-fructose with
some unhydrlized sucrose
© Paul Skelcher/Rainbow
Return to TOC
Section 18.13
Disaccharides
Practice Exercise
• Which of the monosaccharides maltose, cellobiose, lactose, and

sucrose has each of 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.
Answers:

a. Lactose, sucrose
b. Maltose, cellobiose, lactose, sucrose
c. Sucrose
Return to TOC
d. Sucrose
Section 18.14
General Characteristics of Polysaccharides
The Polymer Chain

• Polymers
• Many monosaccharide units bonded with glycosidic linkages
• Two types:
- Linear and branched, homo- and hetero-polysaccharides
Return to TOC

Section 18.14
General Characteristics of Polysaccharides
• Polysaccharides are not sweet and don’t show positive

tests with Tollen’s and Benedict’s solutions whereas
monosaccharides are sweet and show positive tests
• Limited water solubility
• Examples:
– Cellulose, starch in plants
– Glycogen in animals
– Chitin in arthropods
Return to TOC

Section 18.15
Storage Polysaccharides
Starch
• A storage polysaccharide is a polysaccharide that is a
storage form for monosaccharides and is used as an
energy source in cells.
• Starch:
– Glucose is the monomeric unit
– Storage polysaccharide in plants
– Two types of polysaccharidse isolated from starch:
– Amylose: Straight chain polymer - 15 - 20% of the
starch and has α (1  4) glycosidic bonds
– Molecular Mass: 50,000 (up to 1000 glucose units)
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Section 18.15
Amylopectin Stucture
• Amylopectin:
– Branched chain polymer - 80 - 85 % of the starch α
(14) glycosidic bond for straight chain and α (16)
for branch
– Molecular Mass: 300,000 (up to 100,000 glucose
units) - higher than amylose
– Human can hydrolyze alpha linkage but not beta
linkage
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Section 18.15
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Section 18.15
Glycogen
– Humans and animals storage polysaccharide
– Contains only glucose units
– Branched chain polymer – a (14) glycosidic bonds in
straight chains and a (16) in branches
– Molecular Mass: 3,000,000 (up to 1,000,000 glucose
units)
– Three times more highly branched than amylopectin in
starch
– Excess glucose in blood stored in the form of glycogen
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Section 18.15
Figure 18.2 5: The small, dense particles within
this electron micrograph of a liver cell are
glycogen granules
Dr. Dennis Kunkel/Phototake
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Section 18.16
Structural Polysaccharides
Cellulose
• Linear homopolysaccharide with b (1  4) glycosidic bond
• Up to 5000 glucose units with molecular mass of 900,000 amu
– Cotton ~95% cellulose and wood ~50% cellulose
– Humans don’t have enzymes that hydrolyze b (1  4) - so humans
can not digest cellulose -- animals also lack these enzymes but they
can digest cellulose because they have bacteria in their guts to
hydrolyze cellulose
– It serves as dietary fiber in food-- readily absorbs water and results in
softer stools HO
– 20 - 35 g of dietary fiber is desired everyday O HO O
OH
HO O O
OH (1-4) OH
O O
HO
OH  (1-4)
O O OH
OH (1-4)
O OH
OH Return to TOC

Section 18.16
Figure 18.2 6: A sandwich such as this is high in dietary
fiber, that is, it is cellulose-rich "meal"
© Steven Needham/Envision
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Section 18.16
Chitin
– Similar to cellulose in both function and structure
– Linear polymer with all b (14) glycosidic linkages - it has a N-
acetyl amino derivative of glucose
– Function is to give rigidity to the exoskeleton s of crabs, lobsters,
shrimp, insects, and other arthropods
HO
HO O O
OH
HO O
O NAcetyl
OH HN
O O DGlucoseamine
HO
OH HN O
O O
O OH HN O
HN O
O
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Section 18.16
Figure 18.2 7: Chitin, a linear β (1-4)
polyssacharide, produces the rigidity in the
exoskeletons of crabs and other anthropods.
© Don Kreuter/Rainbow
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Section 18.17
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.
• Structural polysaccharide present in connective tissue
associated with joints, cartilage, synovial fluids in animals and
humans
– Primary function is lubrication necessary for joint
movement
– These are heteropolysaccharides - have more than one
type of monosaccharide monomers is present.
• Examples:
– Hyaluronic acid
– Heparin
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Section 18.17
Figure 18.2 9: Acidic polysaccarides, associated
with the connective tissue of joints give hurdlers
the flexibility needed to accomplish their task.
J.M. Barey/Vandystadt/Photo Researchers
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Section 18.17
Hyaluronic Acid and Heparin

• Hyaluronic acid:
– Alternating residues of N-
acetyl-b-D-glucosamine and
D-glucuronic acid.
– Highly viscous - serve as
lubricants in the fluid of
joints and part vitreous
humor of the eye.
• Heparin:
– An anticoagulant-prevents
blood clots.
– Polysaccharide with 15–90
disaccharide residues per
chain.
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Section 18.18
Glycolipids and Glycoproteins: Cell Recognition
• A glycolipid is a lipid molecule that has one or more

carbohydrate (or carbohydrate derivative) units
covalently bonded to it.
• A glycoprotein is a protein molecule that has one or

more carbohydrate (or carbohydrate derivative) units
covalently bonded to it.
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Section 18.19
Dietary Considerations and Carbohydrates
Nutrition
• Foods high in carbs content constitute over 50% of the diet of most
people of the world -- a balanced dietary food should contain about
60% of carbohydrate:
– Corn in South America
– Rice in Asia
– Starchy root vegetables in parts of Africa
– Potato and wheat in North America
• Nutritionist divide dietary carbs into two classes:
– Simple carb: dietary monosaccharides or disaccharides - sweet
to taste commonly referred to as sugars - 20 % of the energy in
the US die
– Complex carbs: Dietary polysaccharides -- starch and cellulose -
normally not sweet to taste
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Section 18.19
Glycemic Foods
• A developing concern about intake of carbohydrates
involves how fast the given dietary carbs are broken
down to glucose within the human body
• Glycemic effect refers to:
– how quickly carbs are digested
– how high blood glucose rise
– how quickly blood glucose levels return to normal
• Glycemic index (GI) has been developed for rating foods
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Section 18.19
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Section 18.19
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BIOCHEMISTRY

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Carbohydrates

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The Study of Living Things

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The Study of Living Things

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Figure 18.1: Biochemical Substances, Mass

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Functions of Carbohydrates in the Human Body

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Objects and Mirror Images

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The property of handedness is not restricted to carbohydrates. It is a

• Chiral Center: C atom attached to 4 different groups bonded to it

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four DIFFERENT groups.

E. g. 3-bromopentane - C has two CH -CH groups – so it is achiral . A

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Copyright © Cengage Learning. All rights reserved c. Chiral center 20

Responses of Left and Right Handed Forms of

– Both may be active, one may be more active or one

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Figure 18.6: (a) Enantiomers and (b)

Figure 18.8: The German

Fischer Project Formulas

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Fischer Project Formulas

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Fischer Project Formulas

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Fischer Project Formulas

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Constitutional Isomers and Diastereomers

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Interaction of Enantiomers with Plane-Polarized Light

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Dextrorotary and Levorotatory Compounds

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Interactions Between Chiral Compounds

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Interactions Between Chiral Compounds

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Figure18.11: Spearmint leaves contain L-

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Most Common Monosaccharides

• Example: CHO CH2OH

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Glucose and Fructose

H OH 1. Most abundant in nature

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Figure 18.15: A 5% (m/v)

Galactose and Ribose

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