BIOCHEMISTRY

CARBOHYDRATES
 Biochemistry
Learning Outcomes:
a. Define biochemistry in his own words.
b. Discuss the scope of Biochemistry and its
relevance in todays world.
c. Define and classify carbohydrates based on
composition and structures.
d. Become familiar with stereoisomerism.
 Biochemistry: An Overview
• Biochemistry - study of 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.
- divided into two groups: Bioinorganic
substances and Bioorganic substances.
Biochemistry: An Overview

Mass composition data for the human body

 Carbohydrates: Occurence &
Functions
• Carbohydrates - most abundant class of
bioorganic molecules in the planet
- constitute about 75% by mass of dry
plant materials.
• Photosynthesis - process used by green
(chlorophyll-containing) plants to
produce carbohydrates.
 Carbohydrates: Occurence &
Functions
Photosynthesis:
chlorophyll
CO2 + H2O + solar energy Carbohydrates + O2
Plant Enzymes
 Carbohydrates: Occurence &
Functions
• Functions of Carbohydrates in humans:
1. Carbohydrate oxidation provides energy.
2. Carbohydrate storage, in the form of glycogen, provides
a short-term energy reserve.
3. Supply carbon atom for the synthesis of other
biochemical substances.
4. Form part of the structural framework of DNA and RNA
molecules.
5. Carbohydrates linked to lipids are structural components
of cell membranes.
6. Carbohydrates linked to proteins function in a variety of
cell-cell and cell-molecule recognition processes.
 Classification of Carbohydrates
• Carbohydrates - is a
polyhydroxy aldehyde, a
polyhydroxy ketone, or a
compound that yields
polyhydroxy aldehydes or
polyhydroxy ketones upon
hydrolysis.
• Classified into four groups:
monosaccharide, disaccharide,
oligosaccharide, and
polysaccharide
 Classification of Carbohydrates
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
 Classification of Carbohydrates
Disaccharide
• Contain two monosaccharide units
covalently bonded to each other
• Hydrolysis produces two monosaccharide
units
• Water soluble white crystalline solids
 Classification of Carbohydrates
Oligosaccharide
• Contain three to ten monosaccharide
units covalently bonded to each other
• Complete hydrolysis produces several
monosaccharide molecules
 Classification of Carbohydrates
Polysaccharide
• Contains many monosaccharide units
covalently bonded
• Polymers: May contain 100s of 1000s of
monosaccharide units
• Undergo hydrolysis to produce
monosaccharides.
 Chirality: Handedness in Molecules
• Most monosaccharides exhibit handedness
that is they exist in two forms. However this
property of handedness is not limited to
carbohydrates only. It is a general
phenomenon found in all classes of organic
compounds
 Chirality: Handedness in Molecules
• Most monosaccharides exhibit handedness
that is they exist in two forms. However this
property of handedness is not limited to
carbohydrates only. It is a general
phenomenon found in all classes of organic
compounds
 Chirality: Handedness in Molecules
MIRROR IMAGES:

• ALL objects as well as molecules have mirror

images

• Mirror Image – reflection of an object in a mirror

• Objects can be divided into two classes on the

basis of their mirror images
 Chirality: Handedness in Molecules
Classes of objects:
1.] Superimposable mirror images
- images that coincide at all points when the images are laid upon
each other
- Ex. Erlenmeyer flask

2.] Nonsuperimposable mirror images

- images where not all points coincide when the images are laid upon
each other
- Ex. Human hands
 Chirality: Handedness in Molecules
CHIRAL
• Molecules that are not superimposable with their
mirror images are said to be chiral (from the
Greek word cheir – hand)

• Chiral Molecule - molecule whose mirror image is

not superimposable

• Achiral Molecule - molecule whose mirror image

is superimposable
 Chirality: Handedness in Molecules
Example:
a.) glyceraldehyde and its mirror image are
NOT superimposable

b.) methane and its mirror image are superimposable

 Chirality: Handedness in Molecules
• Any organic molecule that contains a carbon
with four different groups attached to it in a
tetrahedral orientation possess handedness
and is a chiral center
• Chiral Center - an atom in a molecule that has
four different groups tetrahedrally bonded to
it .
Chirality: Handedness in Molecules
 Chirality: Handedness in Molecules
Importance of Chirality
• In human body chemistry, right- and left-handed
forms of a molecule often will result to different
responses within the body.
• Sometimes both are present giving different body
responses
• Sometimes the same responses only that the
response of one form is far greater than the other
form.
• Other times only one form is biologically active
 Chirality: Handedness in Molecules
Importance of Chirality
• Naturally occuring monosaccharides are almost
always right-handed.

• Plants (dietary source of carbohydrates) produce

ONLY right-handed monosaccharides.

• Amino acids (building blocks for proteins) are

always left-handed molecules
 Stereoisomerism
• Stereoisomers - isomers that have the same molecular and
structural formulas but differ in the orientation of atoms in
space.

• Two major structural features of stereoisomerism

1. Presence of chiral center in a molecule
2. Presence of structural rigidity in a molecule
Ex. Cis-trans isomerism

• Types of Stereoisomers:
1. Enantiomers
2. Diasteriomers
 Stereoisomerism
Review on isomerism: Types of isomerism
Structural – the same Stereoisomerism – the same
chemical groups being chemical groups are bonded
bonded to different to the same carbon atoms but
carbon atoms in different orientations
 Stereoisomerism
• Enantiomers - stereoisomers whose molecules
are nonsuperimposable
• stereoisomers of a chiral substance that have a
mirror-image relationship
ex. left and right-handed forms of a molecule
with a single chiral center

• NOTE: Enantiomers must have opposite

configurations AT ALL chirality centers
 Stereoisomerism
• Diastereomers
• a term that indicates the relationship between
non-mirror image stereoisomers
• stereoisomers whose molecules are not mirror
images of each other
• ex. Cis and trans isomers

• NOTE: Diastereomers have the same

configuration at one or more chiral centers but
differ at other chiral centers.
 Fischer Projection Formulas
• Fischer projection formulas - two-dimensional
structural notation for showing the spatial
arrangement of groups about chiral centers in
molecules
• a means of showing the absolute
configuration of chiral molecules on a flat
page.
• uses a cross to represent the chirality center
 Fischer Projection Formulas
• horizontal arms of the cross represent bonds
coming out of the plane of the slide
• vertical arms of the cross represent bonds
going back into the plane
 Fischer Projection Formulas
• D-L system – applies only for stereoisomers
attached to 2 different C substituents (R and
R’), a H, and X (heteroatom; OH or NH2)
• R and R’ are vertical while H and X are
horizontal
 Fischer Projection Formulas
• One enantiomer is distinguished from the
other by using the prefixes D (dextro; right)
and L (levo; left)
• ex. glyceraldehyde

CHO CHO
H OH HO H
CH2OH CH2OH
D-Glyceroldehyde L-Glyceroldehyde
(-OH on right side) (-OH on left side)
Q: What is the D and L designation of a molecule with more
than 1 chiral center?
For compounds with more than one chiral center, the
HIGHEST numbered chiral center determines the D or L
configuration of the molecules

How many enantiomers and diastereomers exist in 2,3,4-

trihydroxybutanal. Label them as D or L isomers.
 Fischer Projection Formulas
• * 2,3,4-trihydroxybutanal have 2 enantiomeric pairs and 4
diastereomeric pairs

• For compounds with more than one chiral center, the

HIGHEST numbered chiral center determines the D or L
configuration of the molecules

• Epimers – diastereomers whose molecules differ only in the

configuration at one chiral center

Note: The carbon chain is numbered starting on the carbonyl

group, C=O, of the molecule
Fischer Projection Formulas
Fischer Projection Formulas
 Properties of Enantiomers
• Like constitutional isomers, diastereomers are
also different in most of their chemical and
physical properties (ex. BP and MP)
• Nearly all of the properties of a pair of
enantiomers are the same (ex. Identical BP, MP)
• Enantiomers exhibit different properties in 2
areas ONLY:
1. interaction with plane polarized light
2. interaction with other chiral substances
Interaction of Enantiomers with Plane-Polarized Light:
(Recall: wave-like property of light)
- all light travel through space
with a wave-like motion
Unpolarized light

- Ordinary light waves are

filter
unpolarized waves

- Ordinary light can be

converted to polarized light
by passing it through a
POLARIZER

Second filter
 D-isomer
• When plane of
polarized light is
rotated clockwise

• When plane of
polarized light is
rotated
L-isomer counterclockwise

Extent of rotation depends on:

- concentration and
- Identity of enantiomer
 Properties of Enantiomers
• Dextrorotatory and Levorotatory Compounds:

• enantiomers are optically active

• Optically Active Compound – a compound that

rotates the plane of polarized light

• Rotate the plane of polarized light equally but in

opposite directions
 Properties of Enantiomers
• Dextrorotatory Compound – a chiral compound that rotates
the plane of polarized light in a clockwise direction

• Levorotatory Compound - a chiral compound that rotates

the plane of polarized light in a counterclockwise direction

• a (+) or (-) sign is used to indicate the direction of rotation

of a plane-polarized light by a chiral molecule

Note: Molecular handedness (D and L) are not related to the

direction of rotation of plane polarized light
 Properties of Enantiomers
Interactions Between Chiral Compounds:

• Chirality of a molecule becomes important when

the molecule interacts with another chiral
molecule.

• Enantiomeric pairs have the same interaction

with achiral molecules but have different
interaction with chiral molecules
 Properties of Enantiomers
Interactions Between Chiral Compounds:
1. Enantiomers have the same BPs, MPs, and densities.

- these properties depend the strength of intermolecular

force
- Strength of intermolecular force is the same for both
forms of chiral molecules

2. Enantiomeric pairs have the SAME solubility in an

achiral solvent (ethanol) but DIFFERENT in a chiral solvent
(D-2-butanol).
 Properties of Enantiomers
Interactions Between Chiral Compounds:
3. Rate and extent of reaction of enantiomers with
another reactant are the same if the reactant is ACHIRAL
but different when the reactant is CHIRAL.

4. Receptor sites inside the body have chirality associated

to them.

- Enantiomers always produce different responses within

the human body when they interact such sites.
 Properties of Enantiomers
Ex. Chiral-chiral
interactions in the
human body involving
enantiomers

Taste perceptions:
distinct different
flavors of spearmint
and caraway are
produced by
enantiomeric
molecules that
interacted with chiral
“taste receptors”
 Properties of Enantiomers

Body’s response to
epinephrine
(adrenaline
hormone)
- The body’s
response to the D-
isomer is 20x
greater that of L-
isomer
Classification of Monosaccharides
Monosaccharide
• 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
Classification of Monosaccharides
• Example:
– Aldohexose:
Monosaccharide
with aldehyde group
and 6 C atoms – D-
glucose
– Ketohexose:
Monosaccharide
with ketone group
and 6 C atoms – D-
fructose
Classification of Monosaccharides
 Biochemically Important
Monosaccharides
1.D-glyceraldehyde and Dihydroxyacetone
- Simplest of the monosaccharides
- Important in the processes of glycolysis

Glycolysis – series of reactions by which glucose is

converted into 2 molecules of pyruvate (a C3 molecule)
 Biochemically Important
Monosaccharides
2. D-GLUCOSE
– also called dextrose or blood sugar
- sugar referred to when blood sugar is
measured
- most abundant monossacharide
 Biochemically Important
Monosaccharides
• Ripe fruits: good source of glucose ex. ripe grapes contain
20-30% glucose by mass (- grape sugar)

• building block for the polyssacharides starch and cellulose

• carbohydrate that is transported in the bloodstream

• provides energy for cells during metabolism

• Normal blood glucose level: 70 – 100 mg/dL

 Biochemically Important
Monosaccharides
• Glucose requires no digestion and can be given
intravenously to patients who are unable to
ingest food

• Glucose is also found in the urine of patients with

diabetes mellitus

• Its presence in the urine is called glycosuria.

 Biochemically Important
Monosaccharides
• Insulin & glucagon
-hormones that have important roles in
keeping glucose blood level within the normal
range.
- Abnormal functioning of the hormonal control
process for blood-glucose levels leads to the
condition known as diabetes.
 Biochemically Important
Monosaccharides
3. D- Fructose
• ketohexose found in honey
• also called levulose and fruit sugar
• almost twice as sweet as the normal table sugar with about the
same number of calories per gram
• As such, it is often used as dietary sugar due to its less needed
amount not because it has fewer cal/g compared to other sugar
 Biochemically Important
Monosaccharides
4. D-Galactose
- Also called a brain sugar
– one of the two monossacharides that form lactose
- Differs from D-glucose at carbon-4; thus these 2
sugars are epimers
 Biochemically Important
Monosaccharides
• It is synthesized from glucose in the mammary glands
for use in lactose (milk sugar)
• Also found in chemical markers that differentiates
various types of blood: A, B, AB and O
• Individuals with galactosemia (a rare inherited disease)
lack an enzyme needed to metabolize galactose.
• Galactose accumulates, causing a variety of physical
problems including cataracts, cirrhosis, and mental
retardation
• Galactosemia can be detected in newborn screening
• Affected infants must be given soy-based formula to
avoid milk products with lactose
 Biochemically Important
Monosaccharides
5. D-ribose
• A pentose
• Component of a variety of complex
molecules:
- Ribonucleic acids (RNA)
- Energy-rich compounds like
adenosine triphosphate (ATP)

• * 2-deoxy-D-ribose is important
component in DNA; lacks O-atom
at C2
 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
 Cyclic Forms of Monosaccharides
Cyclic Hemiacetal Forms of D-Glucose
 Cyclic Forms of Monosaccharides
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 2OH
O O OH
5 5
4 1
OH 4 OH
1
2 OH 2
OH OH
3 3
OH OH
-D-Glucose -D-Glucose
 Cyclic Forms of Monosaccharides
• Anomeric Carbon atom – is the hemiacetal carbon
atom present in a cyclic monosaccharide structure.
• It is the carbon atom bonded to an –OH group & to
the oxygen atom in the heterocyclic ring.
• Anomers are cyclic monosaccharides that differ only
in the positions of the substituents on the anomeric
carbon atom.
 Cyclic Forms of 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.
 Cyclic Forms of Monosaccharides
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

OH CH2OH CH2OH CH2OH

O O
OH OH
OH
OH
-D-Glucose OH OH
OH OH
OH
 -D-Fructose  -D-Ribose
Pyranose Furanoses
 Haworth Projection Formulas
• 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 CH2OH
CH2OH CH2 OH
O O
OH
OH
OH OH
OH OH
OH OH
OH OH
-D-Glucose  -D-Fructose  -D-Ribose
 Haworth Projection Formulas
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.
 Haworth Projection Formulas
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.
 Reactions of Monosaccharides
Five important reactions of monosaccharides:
1. Oxidation to acidic sugars
2. Reduction to sugar alcohols
3. Glycoside formation
4. Phosphate ester formation
5. Amino sugar formation
• These reactions will be considered with respect
to glucose.
• Other aldoses, as well as ketoses, undergo similar
reactions.
 Reactions of Monosaccharides
• 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.
 Reactions of Monosaccharides
• 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.
 Reactions of Monosaccharides
• 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.
 Reactions of Monosaccharides
• 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 or
alditol.
• D-glucitol known by the common name D-Sorbitol – is used as
moisturizing agents in foods and cosmetics and as a sweetening agent in
chewing gum.
 Reactions of Monosaccharides
• 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
 Reactions of Monosaccharides
• 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.
 Reactions of Monosaccharides
• 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
 Reactions of Monosaccharides
• Amino sugars and their N-acetyl derivatives are important
building blocks of polysaccharides such as chitin and
hyaluronic acid.
• N-acetyl derivatives of D-glucosamine and D-galactosamine
are present in the biochemical markers on red blood cells
which distinguish various blood types.
 Reactions of 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.
 Reactions of Monosaccharides
• 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.
Reactions of Monosaccharides
 Disaccharide
• Two monosaccharides can react to form disaccharide
• One monosaccharide act as a hemiacetal and other as alcohol
• Glycosidic linkage- is the bond between two monosaccharides
resulting from the reaction between the hemiacetal carbon –
OH group of one monosaccharide and an –OH group on the
other monosaccharide.
• It is always a carbon-oxygen-carbon bond in a disaccharide.
 Disaccharide
• Cellobiose is produced as an intermediate in
the hydrolysis of the polysaccharide cellulose:
• Cellobiose contains two b - D-glucose
monosaccharide units linked through a b (1—
4) glycosidic linkage.
CH2OH
O OH
CH2OH  (1-4)
H
O OH
O
OH
OH
OH
OH
Cellobiose
 Disaccharide
• Maltose
- malt sugar
- produced whenever the polysaccharide
starch breaks down, as happens in plants
when seeds germinate and in human
beings during starch digestion.
 Disaccharide
• Maltose is digested easily by humans because
we have enzymes that can break a (1-4)
linkages but not b (1-4) linkages of cellobiose.
Therefore cellobiose cannot be digested by
humans.
CH2 OH CH2 OH

O O

OH OH
O OH
OH

OH OH

Maltose
 Disaccharide
• Lactose is made up of b-D-galactose unit and a
b-D-glucose unit joined by a b(1-4) glycosidic
linkage
 Disaccharide
• 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 b(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.
 Disaccharide
• Sucrose (table sugar): The
most abundant of all
disaccharides and found in
plants.
• It is a non-reducing sugar
• It is 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
 Oligosaccharide
• Oligosaccharides are
carbohydrates that
contain three to ten
monosaccharide units
bonded to each other
via glycosidic linkage.
• Two naturally occuring
oligosaccharides:
raffinose
(trisaccharide) and
stachyose
(tetrasaccharide)
 General Characteristics of
Polysaccharides
• Polymers
• Many
monosaccharide
units bonded with
glycosidic linkages
• Also called glycans
• Two types:
• - Linear and
branched, homo-
and hetero-
polysaccharides
 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
 Storage Polysaccharides
• 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 & Amylopectin
Amylose: Straight chain polymer - 15 - 20% of the
starch and has a (1 → 4) glycosidic bonds
Molecular Mass: 50,000 (up to 1000 glucose units)
 Storage Polysaccharides
• Amylopectin:
- Branched chain polymer - 80 - 85 % of
the starch a (1→4) glycosidic bond for
straight chain and a (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
 Storage Polysaccharides
• Iodine:
- used to test the presence of starch in
solution
- starch containing solutions turn a dark
blue-black when iodine is added.
 Storage Polysaccharides
• 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
 Structural Polysaccharides
• Structural Polysaccharide
polysaccharide that serves as structural
element in plant cell walls and animal
exoskeleton
 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
HO
results in softer stools
HO O O
- 20 - 35 g of dietary fiber is desired everyday OH
HO O O
OH (1-4) OH
HO O O
OH  (1-4)
O O OH
OH (1-4)
O OH
OH
 Structural Polysaccharides
• 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 exoskeletons of crabs,
lobsters, shrimp, insects, and other arthropods
HO

HO O O
OH
O
HO
OH
O
HN
N-Acetyl
HO
O O -D-Glucosamine
OH HN O
O O
O OH HN O

HN O

O
 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
 Acidic Polysaccharides
Hyaluronic Acid and Heparin
• Hyaluronic acid:
- Alternating residues of N-
acetyl-b-D-glucosamine and D-
glucuronate
- 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.
 Dietary Considerations &
Cabohydrates
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 diet
- Complex carbs: Dietary polysaccharides -- starch and
cellulose - normally not sweet to taste
 Dietary Considerations &
Cabohydrates
• Natural Sugar - is a sugar naturally present in whole foods.
Example: Milk and fresh fruit
• Refined Sugar - is a sugar that has been separated from its plant
source.
Example: sugar beets and sugar cane
• Refined sugars are often said to provide empty calories since they
provide energy but few other nutrients.
• Natural sugars on the other hand are accompanied by nutrients.
• Grains- major dietary source for complex carbohydrates n the U.S.
diet.
-Source of both starch and fiber as well as protein, vitains, and minerals.
Potato pulp provides starch and the skin provides fiber.
Broccoli and green beans are low in starch but high in fiber.
 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.