MC2

Biochemistry
BSN-1
ROLINA M. CABALLERO, RN
Whatever you do,
do it all for the
glory of God.
- 1 Corinthians 10:31
BSN
1I
B
SN
1J 01
Carbohydrates
Chapter contents

Occurrence and
1.1 Biochemistry- An 1.2 Functions of
overview Carbohydrates

Chirality:
Classifications of Handedness in
1.3 Carbohydrates
1.4
Molecules
 Stereoisomerism: Designating
Enantiomers and Handedness Using
1.5 1.6 Fischer Projection
Diastereomers
Formula

Properties of Classifications of
1.7 Enantiomers
1.8
Monosaccharides
 Biochemically
Important Cyclic Forms of
1.9 1.10 Monosaccharides
Monosaccharides

Haworth
Projection Reactions of
1.11 Formulas
1.12
Monosaccharides
1.13 Disaccharides 1.14 Oligosaccharides

General
Characteristics of Storage
1.15 Polysaccharides
1.16 Polysaccharides
 Structural Acidic
1.17 Polysaccharides 1.18 Polysaccharide

Dietary
Glycolipids and
Considerations
1.19 1.16 Glycoproteins:
and
Cell Recognition
Carbohydrates
 Learning Objectives

1.1 Distinguish between

bioinorganic and bioorganic
substances; be able to list
the major classes of
bioorganic substances.
 1.1 Biochemistry- An overview
- 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 (70%) and inorganic salts 5%(e.g.

NaCl, KCI)
● Bioorganic substances- Carbohydrates 2%, lipids 8%, proteins 15%,
nucleic acids 2%
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.
 Learning Objectives
1.2 Know the major source
of and the major functions
for carbohydrates in the
human body.
 1.2 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
 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
 Photosynthesis

● Process in which plants produce

carbohydrates using carbon dioxide, water, and
solar energy
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
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
 Learning Objectives
1.3 Be able to differentiate among
the carbohydrates classification
monosaccharides, disaccharides,
oligosaccharides, and
polysaccharides; be familiar with
the functional groups present in
carbohydrate molecules
Classifications of Carbohydrates
● Empirical formula of simple carbohydrates

● Carbohydrate: Polyhydroxy aldehyde, ketone, or

a compound that produces such substances
upon hydrolysis
 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
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
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
 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
 Learning Objectives
1.4 Be familiar with the
concepts of handedness as it
applies to monosaccharides;
be able to classify molecules
as chiral or achiral and to
identify chiral centers
present in chiral molecules.
 1.4 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
 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)
 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
 Practice Exercise
● Indicate whether the circled carbon atom in each
of the following molecules is a chiral center.
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
● Proteins are often enantioselective towards their binding
partners. When designing small molecules to interact
with these targets, one should consider stereoselectivity.

● The purpose of a drug discovery and development

project is to find new therapeutic agents that target a key
enzyme, protein-protein interaction, receptor-ligand, or
protein-nucleic acid interaction of relevance in a disease
of interest in order to mitigate the course of the disease.
Finding compounds that can, for example, bind to the
active site of an enzyme and inhibit its normal activity is
merely the initial goal in most drug discovery projects.
 Learning Objectives
1.5 Distinguish between the
concepts of stereoisomerism
and constitutional isomerism;
distinguish between
stereoisomers called
enantiomers and those called
diastereomers.
 Isomers are molecules that share a molecular
formula but differ either in the order of bonds or the
orientation of bonded groups in space.

- Are two or more different substances with the

same molecular formula.

- Despite having the same molecular formula, the

physical properties of each molecule may differ,
particularly if the functional groups associated
with each molecule are different.
1.5 Stereoisomerism: Enantiomers and
Diastereomers
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
Constitutional Isomerism (Structural)
● Structural (constitutional) isomers have the
same molecular formula but a different
bonding arrangement among the atoms.
Enantiomers
 Learning Objectives
1.6Be familiar with the
procedures for drawing
Fischer projection formulas
for monosaccharides; be
able to recognize the D-form
and L-form of a
monosaccharide given its
Fischer projection formulas.
 1.6 Designating Handedness Using
Fischer Projection 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
A different way of visualizing a molecule
The stereogenic Carbon are implied
Fischer Project Formulas
● L and D system used to designate the
handedness of glyceraldehyde enantiomers are
shown below
• 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
• 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
 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
Learning Objectives
1.7 Contrast enantiomers in
terms of their interactions with
plane-polarized light and their
interactions with other chiral
substances.
 1.7 Properties of Enantiomers
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
Figure 18.10 - Vibrational Characteristics of Ordinary
Light and Plane-Polarized Light
Dextro rotary 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
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
• 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
Carbohydrates are optically active compounds
because it will rotate the plane of polarized
light.
Learning Objectives
1.8 Be able to classify
monosaccharides by the number of
carbon atoms present and by the
types of carbonyl groups present.
1.8 Classification of 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
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
 Learning Objectives
1.9 Be able to distinguish
among, based in structural
characteristics, the
monosaccharides
glyceraldehyde,
dihydroxyacetone, glucose,
galactose, fructose, and ribose.
 1.1 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
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
● A comparison of the Fischer projection formulas for
d-galactose and d-glucose shows that these two
compounds differ only in the configuration of the -OH
group and -H group on carbon 4.
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
From the third to the sixth carbon, the structure
of d-fructose is identical to that of d-glucose.
Differences at carbons 1 and 2 are related to the
presence of a ketone group in fructose and of an
aldehyde group in glucose.
 D-Ribose
• Part of a variety of complex
molecules which include:
– RNA
– ATP
– DNA
• Five-membered cyclic form
d-Ribose is a pentose. If carbon 3 and its
accompanying -H and -OH groups were eliminated
from the structure of d-glucose, the remaining
structure would be that of d-ribose.
- The compound 2-deoxy-d-ribose is also important
in nucleic acid chemistry. Component of the DNA
molecules.
- The prefix deoxy- means “minus an oxygen”; the
structures of ribose and 2-deoxyribose differ in
that the latter compound lacks an oxygen atom at
carbon 2
d-Glyceraldehyde and Dihydroxyacetone
● The simplest of the monosaccharides, these two
trioses are important intermediates in the process
of glycolysis; a series of reactions whereby glucose
is converted into two molecules of pyruvate.
● d-Glyceraldehyde is a chiral molecule, but
dihydroxyacetone is not
 Learning Objectives

1.10 Be able to use Haworth

projection formulas to denote
the cyclic forms of
monosaccharides
 1.10 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
Figure 18.17 - The Cyclic Hemiacetal Forms of D-Glucose
Cyclic Hemiacetal Forms of D-Glucose
• 2 forms of D-Glucose: (Anomers) *position
– 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

– α-form – β-form
Special Terminology for Cyclic Monosaccharide Structures

● anomeric carbon atom- is the hemiacetal carbon

atom present in a cyclic monosaccharide structure. It
is the carbon atom that is bonded to an -OH group and
to the oxygen atom in the heterocyclic ring.
Special Terminology for Cyclic Monosaccharide Structures
●
Anomers are cyclic monosaccharides that differ only in
the positions of the substituents on the anomeric
(hemiacetal) carbon atom.
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
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
Monosaccharides in nature have cyclic forms
because they can form internal hemiacetals
that are stable.
 Learning Objectives

1.11 Be able to convert

Fischer projection formulas
Haworth projection formulas
 1.11 Haworth Projections Formulas

• Two-dimensional structural notation that specifies

the three-dimensional structure of a cyclic form of a
monosaccharide
 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
 –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
 Learning Objectives
1.12 Be familiar with the
characteristics of the following
types of monosaccharides
chemical reactions: oxidation,
reduction, glycoside formation,
phosphate ester formation, and
amino sugar formation.
 1.12 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
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
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
 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
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
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
 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
 Learning Objectives
1.13 For the disaccharides maltose,
cellobiose, lactose, and sucrose, be
able to specify (1) the
monosaccharide unit present, (2)
the type of glycosidic linkage
present, and (3) whether or not the
disaccharide is a reducing sugar.
 1.13 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
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
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.
 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
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
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
 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
 Learning Objectives
1.14 Describe the structural
features of and occurrence of
the oligosaccharides raffinose
and stachyose
and the
oligosaccharide-containing
substance solanine
 1.14 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
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
• 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
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
 Learning Objectives

1.15 Know the important general

parameters that distinguish
various polysaccharides from
each other.
 1.15 General characteristics of
Polysaccharides

• Polysaccharides are polymers of many

monosaccharide units bonded with glycosidic
linkages
• Two types:
– Homopolysaccharide
– Heteropolysaccharide
Figure 18.26 - The Polymer Chains of a Polysaccharide
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
 Learning Objectives
1.16 Describe the structural
feature of the storage
polysaccharides starch and
glycogen contrast the
biochemical functions of the
starch and glycogen.
 1.16 Storage Polysaccharides

• 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
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)
 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
• Excess glucose in blood is stored in the form of
glycogen
 Learning Objectives

1.17 Describe the structure

features of the structural
polysaccharides cellulose and
chitin, contrast the biochemical
functions of cellulose and chitin
 1.17 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
• It serves as dietary fiber in food and readily absorbs
water resulting in softer stools
– 20–35 g of dietary fiber is desired everyday
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
Figure 18.32(b) - The Structure of Chitin
 Learning Objectives

1.18 Describe the structural

features if the acidic
polysaccharides hyaluronic acid
and heparin: contrast the
biochemical functions of
hyaluronic acid and heparin.
 1.18 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
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
 Heparin
• Polysaccharide with 15–90 disaccharide residues per
chain
• Blood anticoagulant
Learning Objectives
1.9 Contrast the dietary
carbohydrates classifications simple
carbohydrate and complex
carbohydrate: contrast the terms
natural sugar and refined sugar.
 1.19 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
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
Learning Objectives
1.20 Know the general
structural characteristics for
Glycolipids and Glycoproteins:
be familiar with several roles
that glycolipids and
glycoproteins have in cell
recognition processes.
 1.20 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
Reference