CHEMISTRY AND

BIOCHEMISTRY OF
CARBOHYDRATES

1
Carbohydrates are the most abundant organic
compounds on earth.

The amount of cellulose in plants is estimated at

about 1011 tons, and the amount of chitin in
arthropods at about 109 tons.

However, carbohydrates constitute only about 1% of

the mammalian body.

2
Complex storage carbohydrates include starch in
plants, and glycogen in animals.
A normal large dog, for example:
100 gm of glucose stored as liver glycogen,
250 gm as muscle glycogen,
25 gm as adipose tissue glycogen,
10 gm as free glucose in the extracellular fluid
compartments.

3
At rest, between 160-200 gm of glucose are
metabolized per day, with the brain being the
major consumer (~~120 gm/day).

In addition, with increasing time after a meal,

glucose synthesis from noncarbohydrate sources,
predominantly glucogenic amino acids, glycerol,
pyruvate, lactate, and propionate (in herbivores),
gains steadily in importance.

4
 Carbohydrates
Structure and Biological Function

Carbohydrates are chemically defined

as aldehyde or ketone or derivatives of the
higher polyhydric alcohols, or compounds
which yield these derivatives on hydrolysis
or as a polyhydroxy aldehydes or
polyhydroxy ketones

5
 Carbohydrates

Compounds containing C, H and O

General formula : Cx(H2O)y

All have C=O and -OH functional groups.

Classified based on
• Size of base carbon chain
• Number of sugar units
• Location of C=O
• Stereochemistry
6
 Types of carbohydrates

Classifications based on number of sugar units in

total chain.
Monosaccharides - single sugar unit
Disaccharides - two sugar units
Oligosaccharides - 2 to 10 sugar units
Polysaccharides - more than 10 units
Chaining relies on ‘bridging’ of oxygen atoms
glycoside bonds

7
The word saccharide is derived from the Greek
“Sakcharon” meaning “Sugar”

8
 Monosaccharides

Monosaccharides Monosaccharides are simple

sugars that may become basic units of more
complex molecules. They are single chains of
carbon atoms bearing multiple adjacent hydroxyl
groups.
Those with 3-7 carbon atoms are the most important
for mammalian metabolism. Glyceraldehyde and
dihydroxyacetone are trioses (3-carbon atoms),
ribose is a pentose (5-carbon atoms), while
glucose, fructose, and galactose are hexoses (6-
carbon atoms)
9
Glyceraldehyde is the smallest aldose, and
dihydroxyacetone the smallest ketose.

Monosaccharides such as galactose, glucose, ribose, and

fructose do not usually exist in linear form. Instead
they condense into rings of five or six carbon atoms
called furanose or pyranose rings, respectively.

10
Hexoses of glucose, fructose, and galactose are
physiologically the most important.
Glucose is a major mammalian fuel, found widely in
fruits and vegetables as a monosaccharide, in
disaccharides such as sucrose, maltose, and
lactose, and in polysaccharides such as glycogen
and starch.

11
It is converted to other carbohydrates having highly
specific functions (e.g., glycogen for storage, ribose in
nucleic acids, galactose in lactose of milk, in certain
complex lipids, and in combination with protein in
glycoproteins).

Diseases associated with glucose metabolism include

(among others), diabetes mellitus, galactosemia, and
glycogen storage diseases.

12
Fructose is a 6-carbon ketose found in fruit and
honey as a monosaccharide, and in sucrose (a
disaccharide of fructose and glucose).

Diets high in sucrose can lead to large amounts of

fructose entering the hepatic portal vein.

13
In some animals a significant amount of fructose resulting
from the digestion of sucrose is converted to glucose in
the intestinal wall prior to passage into the portal
circulation.
Free fructose is found in seminal plasma, and is secreted
in quantity into the fetal circulation of ungulates and
whales, where it accumulates in amniotic and allantoic
fluids. In all of these situations, free fructose represents
a potential source of fuel.

14
Galactose is a component of lactose (milk sugar), which is
synthesized in mammary glands.
Galactose is found in some vegetable polysaccharides, and
is convertible to glucose in the body (mainly in the liver
where it is almost entirely removed from the portal
circulation following absorption from the intestine).
Galactose also forms part of the polysaccharide chain of
many glycoproteins

15
 Monosaccharides

Based on location of C=O

H CH2OH
| |
C=O C=O
| |
H-C-OH HO-C-H
| |
H-C-OH H-C-OH
| |
H-C-OH H-C-OH
| |
CH2OH CH2OH

Aldose Ketose
- aldehyde C=O - ketone C=O
16
 Monosaccharide classifications

Number of carbon atoms in the chain

H
H |
H | C=O
H | C=O |
| C=O | H-C-OH
C=O | H-C-OH |
| H-C-OH | H-C-OH
H-C-OH | H-C-OH |
| H-C-OH | H-C-OH
CH2OH | H-C-OH |
CH2OH | H-C-OH
|
CH2OH
CH2OH
triose tetrose pentose hexose
Can be either aldose or ketose sugar.
17
 Examples

CH2OH
|
C=O
H |
| HO-C-H
C=O |
| H-C-OH
H-C-OH |
| H-C-OH
|
CH2OH
CH2OH
D-glyceraldehyde D-fructose
triose hexose
aldose ketose
aldotriose sugar ketohexose sugar
18
 Examples
H
|
H C=O
| |
C=O H-C-OH
| |
H-C-OH H-C-OH
| |
H-C-OH HO-C-H
| |
H-C-OH HO-C-H
| |
CH2OH CH2OH
D-ribose L-mannose
pentose, aldose hexose, aldose
aldopentose sugar aldohexose sugar
19
 Stereoisomers

Stereochemistry
Study of the spatial arrangement of molecules.

Stereoisomers have
• the same order and types of bonds.
• different spatial arrangements.
• different properties.
Many biologically important chemicals, like sugars, exist
as stereoisomers.

20
 Enantiomers

Pairs of stereoisomers
Designated by D- or L- at the start of the name.
They are mirror images that can’t be overlapped.

If you don’t believe it,

give it a try!
21
Enantiomers

22
 L- and D- glyceraldehyde

CHO CHO
HO H H OH

C C

CH2 OH CH2 OH

CHO CHO

HO H H OH

CH2 OH CH2 OH
23
 Enantiomers

Chiral center.
Asymmetric carbon - 4 different things are
attached to it.
Cl
|

I- C - F
| Chiral center
Br
You must have at least one asymmetric carbon to
have stereoisomers.
24
Enantiomer are stereoisomers that are
mirror images of each other that are non-
superposable (not identical), much as one's
left and right hands are the same except for
opposite orientation

25
Sterioisomers: Sterioisomers are a subset of
isomers.

Like isomers, stereoisomers are compounds with the

same molecular formula but different molecular
structures.

Stereoisomers must contain an asymmetric carbon

atom.

26
 Epimers

Epimers are stereoisomers that differ in the

orientation of the hydroxide about a single
asymmetric carbon atom.

27
 Examples

Is the ‘red’ carbon chiral?

H H I
Cl
C=O H3C-C-OH C=C
Cl Br F
CH2CH3

H
|
H C=O HH H
|
H3C-C-OH H-C-OH H2N-C-C-C-SH
H | ClH Cl
CH2OH
28
 Physical properties

Optical activity
ability to rotate plane polarized light.

dextrorotatory - rotate to right

- use + symbol
- usually D isomers

levorotatory - rotate to left

- use - symbol
- usually L isomers
29
 Plane polarized light

Light is passed through a polarized filter.

A solution of an optical isomer will rotate the light one
direction.
30
 Some important monosaccharides

D-glyceraldehyde Simplest sugar

D-glucose Most important in diet
D-fructose Sweetest of all sugars
D-galactose Part of milk sugar
D-ribose Used in RNA

note that each is a D- enantiomer

31
 D-glyceraldehyde

Three carbon sugar

Aldose sugar
Triose sugar
H
|
C=O
aldotriose |
H-C-OH
|
CH2OH

32
 D-glucose
• Glucose is an aldohexose sugar.
• Common names include dextrose, grape O
H
sugar, blood sugar. C
H C OH
• Most important sugar in our diet.
HO C H
• Most abundant organic compound H C OH
found in nature. H C OH
• CH2OH
Level in blood can be as high as 0.1%

33
 D-fructose

CH2OH
Another common sugar. |
C=O
|
HO-C-H
It is a ketohexose. |
H-C-OH
|
H-C-OH
Sweetest of all sugars. |
CH2OH

34
 Carbohydrates in cyclic structures

If optical isomers weren’t enough, sugars also form rings.

For many sugars, its the most common form.
hemiacetal - forms from alcohol and aldehyde
hemiketal - forms from alcohol and ketone

R
OR’’
\ |
C=O + ROH R-C
- OH
/ | 35
36
37
 Intramolecular cyclization

Cyclization.
Remember - chains can bend and rotate.

CH2OH CH2OH
H
C OH C O

C C O C C OH

C C C C

38
 Intramolecular cyclization

The -OH group that forms can be above or below the

ring resulting in two forms - anomers
 and  are used to identify the two forms.
·  - OH group is down compared to CH2OH
(trans).
·  - OH group is up compared to CH2OH (cis).

39
 Cyclization of D-glucose
CH2OH  -D - glucose
H O H
H
O OH H
H
C OH OH
H C OH H OH
HO C H
H C OH CH2OH  - D - glucose
H C OH H O OH
H
CH2OH OH H
OH H
H OH
40
 Fischer vs. Haworth projections

 -D-glucose

H C OH CH2OH
H C OH H O H
H
HO C H O H
OH
H C OH OH OH
HO-CH C H
2 H OH

41
 Cyclization of D-fructose

This can also happen

to ketose sugars. CH2OHO CH2OH
H OH 
CH2OH
H OH
C O
OH H
HO C H
H C OH
H C OH CH2OH O OH
CH2OH H OH 
H
CH2OH
OH H
42
 D-galactose

• Not found in many biological systems

• Common part of lactose - disaccharide
CH2OH
OH O H
H
O OH H
H
C H OH
H C OH H OH
HO C H CH2OH
HO C H O OH
OH
H C OH H
OH H
CH2OH
H H
H OH
43
 D-glucose vs. D-galactose
D-glucose D-galactose
H O H O
C C
H C OH H C OH
HO C H HO C H
H C OH HO C H
H C OH H C OH
CH2OH CH2OH

Can you find a difference? Your body can!

You can’t digest galactose - it must be converted to
glucose first.
44
 D-ribose

An important sugar used

in genetic material. H
|
This sugar is not used as C=O
|
an energy source but is a part H-C-OH
of the backbone of RNA. |
H-C-OH
|
When the C-2 OH is removed, H-C-OH
the sugar becomes |

deoxyribose which is used CH2OH

in the backbone of DNA.

45
 Reactions of glucose
and other monosaccharides
Oxidation-Reduction. Required for their complete
metabolic breakdown.
Esterification. Production of phosphate esters.
Amino derivatives. Used to produce structural
components and glycoprotein.
Glycoside formation. Linkage of monosaccharides to
form polysaccharides.

46
 Oxidation-Reduction.
Aldehyde sugars (reducing sugars) are readily oxidized and will
react with Benedict’s reagent.
H O-
| |
C=O C=O
2+
| + 2 Cu + 5 OH- | + 2 Cu2O + 3H2O
H-C-OH H-C-OH
| |
CH2OH CH2OH
This provides a good test for presence of glucose in urine -
forms a red precipitate.
Other tests - Tollen’s or Fehling’s solutions.

47
 Benedict’s reagent

glu c o s e
0.5% 2%

B e n e dic t's
Re a g e n t

48
 Ketone sugars

Ketones are not easy to oxidize except ketoses.

Enediol reaction.
H O
C H C OH CH2OH
H C OH C OH H C O
HO C H HO C H HO C H
H C OH H C OH H C OH
H C OH H C OH H C OH
CH2OH CH2OH CH2OH
So all monosaccharides are reducing sugars.
49
 Esterification

Esters are formed by reaction of hydroxyl groups

(alcohols) with acids.

O O
R OH + C R' R O C R' + H2O
HO

The hydroxyl groups of carbohydrates react similarly

to alcohols.

50
 Esterification

The most important biological esters of

carbohydrates are phosphate esters.
O O
R OH + HO P OH HO P OH + H2O
OH O-R
Example. Phosphoryl group from ATP forms an ester with D-
glucose, catalyzed by kinases.
kinase
D-glucose + ATP D-glucose-6-phosphate + ADP

51
 Amino derivatives

The replacement of a hydroxyl group on a

carbohydrate results in an amino sugar.
CH2OH CH2OH

H O OH H O OH
H H
OH H OH H
OH H OH H

H OH H NH2

-D-glucose -D-2-aminoglucose
(glucosamine)
52
 Amino derivatives

Uses for amino sugars.

Structural components of bacterial cell walls.
As a component of chitin, a polymer found in the
exoskeleton of insects and crustaceans.
A major structural unit of chondroitin sulfate - a
component of cartilage.
Component of glycoprotein and glycolipids.

53
 Glycoside formation

 or  -OH group of cyclic monosaccharide can

form link with another one (or more).
CH2OH CH2OH

H O OH H O H
glycosidic bond H
OH H H
H
OH
OH H OH OH
H OH OH H
sugar -O- sugar
CH2OH
CH2OH H O H
oxygen bridge H
H
O
o
H
H
OH
OH H OH
OH H
OH H
H OH
+ H2 O
54
 Glycosidic bonds

Type is based on the position of the C-1 OH

 glycosidic bond
- linkage between a C-1  OH and a C-4 OH
 glycosidic bond
- linkage between a C-1  OH and a C-4 OH
 bonds  bonds
O O
O
O
C-4 end can be either up or down depending
on the orientation of the monosaccharide.
55
 Glycosidic bonds

 bonds  bonds

O O

O O

56
 Glycosidic bonds

General format used to describe bond.

(
OH type carbon# of
( or ) first sugar
carbon# of
second sugar )
As we work through the next few examples
this will become clear.

For disaccharides - the sugar is either  or 

based on form of the
remaining C-1 OH.
57
Disaccharides and Trisaccharides

Maltose (or malt sugar) is an intermediate in the

intestinal digestion (i.e., hydrolysis) of glycogen
and starch, and is found in germinating grains (and
other plants and vegetables).

It consists of two molecules of glucose in an α-(1,4)

glycosidic linkage.

58
Trehalose, which contains two molecules of glucose
linked together somewhat differently from maltose, is a
major carbohydrate found in the hemolymph of many
insects. It is also found in young mushrooms, where it
accounts for about 1.5% of their weight.
Cellobiose, the repeating disaccharide unit of cellulose,
has β-(1,4) glycosidic linkages which are broken by
bacterial cellulases, but not by mammalian constitutive
digestive enzymes.

59
Lactose is found in milk, but otherwise does not
occur in nature. It consists of galactose and
glucose in a β -(1,4) glycosidic linkage.

60
Sucrose, or cane sugar, consists of glucose and
fructose linked in an a-(1,2) glycosidic bond. It is
abundant in the plant world, and is familiar as
table sugar.

Sucrose and maltose are readily hydrolyzed by

disaccharidases found in the brush border of the
small intestine.

61
Hydrolysis of sucrose to glucose and fructose is
sometimes called inversion, since it is accompanied
by a net change in optical rotation from dextro to
levo as the equimolar mixture of glucose and
fructose is formed on the mucosal surface.

Therefore, the intestinal brush border enzyme that

hydrolyzes sucrose (i.e., sucrase), is sometimes
called invertase.

62
63
 -Maltose

Malt sugar. Not common in nature except in

germinating grains.
CH2OH CH2OH

H O H H O OH
H H
OH H OH H
O H
OH
H OH H OH

-D-glucose -D-glucose

-D-glucose and -D-glucose,  (1 4) linkage.

64
 -Maltose

It is referred to as -maltose because the unreacted

C-1 on -D-glucose is in the  position.

CH2OH CH2OH

H O H H O OH
H H
OH H OH H
O H
OH
H OH H OH

65
 -Maltose

Uses of -maltose
Ingredient in infant formulas.
Production of beer.
Flavoring - fresh baked aroma.

It is hydrolyzed the in body by:

maltase
maltose + H2O 2 glucose

66
 Cellobiose

Like maltose, it is composed of two molecules of D-

glucose - but with a  (1 4) linkage.

CH2OH

H O OH
H
CH2OH OH H
H
H O O
H
H OH
OH H
OH H

H OH
67
 Cellobiose
CH 2 OH CH 2 OH

H O H H O OH
H
The difference in H
OH H OH H
the linkage results OH
O H

in cellobiose H OH H OH
being unusable maltose,  (1 4)
CH2OH
O OH
We lack an enzyme H
H
H
that can hydrolyze CH2OH OH
H
O O
cellobiose. H
H
H OH
OH H
OH H cellobiose
H OH  (1 4)
68
 Lactose

Milk sugar - dimer of -D-galactose and either the 

or  - D-glucose.
CH2OH CH2OH
O O OH
-Lactose OH
H
H
H
OH H O OH H
H H H

H OH H OH

-D-galactose -D-glucose

 (1 4) linkage,  disaccharide.
69
 Lactose

We can’t directly use galactose. It must be converted

to a form of glucose.

Galactosemia - absence of needed enzymes needed

for conversion.

Build up of galactose or a metabolite like dulcitol

(galactitol) causes toxic effects.

Can lead to retardation, cataracts, death.

70
 Lactose

Lactase
Enzyme required to hydrolyze lactose.
Lactose intolerance
Lack or insufficient amount of the enzyme.

If lactase enters lower

GI, it can cause gas
and cramps.

71
 Sucrose
CH2OH
Table sugar - most
common sugar in all H O H
plants. H
OH H
Sugar cane and beet, are up
to 20% by mass sucrose. OH

Disaccharide of - H OH
O
glucose and -
fructose. CH2OH O

H OH
H CH2OH
(1 2) linkage OH H
72
Sucrose

glucose

fructose

73
 How sweet it is!

Sweetness relative
Sugar to sucrose
lactose 0.16
galactose 0.32
maltose 0.33
sucrose 1.00
fructose 1.73
aspartame 180
saccharin 450
74
 Trisaccharide

A number of trisaccharides also occur free in nature,

and are consumed by animals. Raffinose contains
glucose, fructose, and galactose held together by
both a- and b-glycosidic bonds.
This trisaccharide is found in abundance in sugar
beets, and several other higher plants. Melezitose
contains two molecules of glucose and one of
fructose, and is found in the sap of some
coniferous trees.

75
 Polysaccharides

Carbohydrate polymers
Storage Polysaccharides
Energy storage - starch and glycogen
Structural Polysaccharides
Used to provide protective walls or
lubricative coating to cells - cellulose and
mucopolysaccharides.
Structural Peptidoglycans
Bacterial cell walls
76
 Starch

Energy storage used by plants

Long repeating chain of -D-glucose

Chains up to 4000 units

Amylose straight chain

major form of starch
Amylopectin branched structure

77
Starch, the glucose store of plants, is an
important food source of carbohydrate, and
is found in cereals, potatoes, legumes, and
other vegetables. Starch contains 15 to 20%
amylose, and 80-85% amylopectin. While
both glycogen and starch consist totally of
D-glucose, amylose is nonbranched, and
amylopectin contains about one a-1,6
branch per 30 α-1,4 linkages.
78
 Amylose starch

Straight chain that forms coils  (1 4) linkage.

Most common type of starch.
CH2OH CH2OH CH2OH
CH2OH
O O H H O H
H O H H H H
H H H
H OH H
OH H OH H OH H

O O O
O

H OH H OH H OH
H OH

O O O
O

O O O O
O O O O

O O O O O
O O O

O O O
O

79
 Amylose starch

Example showing coiled structure

- 12 glucose units
- hydrogens and side chains are omitted.

80
 Amylopectin starch

Branched structure due to crosslinks.

CH2OH CH2OH CH2OH
CH2OH
O H O H H O H
H O H H H
H H H
H H
H OH H OH H OH
OH
O O O
O

CH2OH H OH CH2OH H OH CH2

H OH CH2OH H OH

O O H H O H
H O H H H H
H H H
H OH H
OH H OH H OH H

O O O
O

H OH H OH H OH
H OH

 (1 6) linkage
at crosslink
81
 Glycogen

• Energy storage of animals.

• Stored in liver and muscles as granules.
• Similar to amylopectin.
 (1 6) linkage
O

at crosslink
O

O
c
O

O
c O

O
O

O
O

82
Glycogen, the form in which animal tissues
store glucose, has a basic structure that
consists of numerous α-1,4 linked D-
Glucose molecules, and is sometimes
referred to as“ animal starch".

Once in every 11 to 18 linkages, a branching

point occurs via an α-1,6 linkage, which yields a
tree-like structure.
83
 Cellulose

• Most abundant polysaccharide.

•  (1 4) glycosidic linkages.
• Result in long fibers - for plant structure.

CH2OH
CH2OH O
H
CH2OH O H
H O
CH2OH O H OH H
H O
CH2OH O H OH H H
H O
O H OH H H
H O
OH H H OH
H O H
OH H H OH
H
H OH
H
H OH
H OH

84
Cellulose is insoluble in water, and consists
of long, non-branched β-1,4 linked glucose
units strengthened by cross-linked
hydrogen bonds.

Due to β -linkages, cellulose is

non-digestible by enzymes of mammalian
origin (i.e., constitutive enzymes).

85
However, in the digestive tracts of
herbivores, cellulase-containing microbes
attack the β-linkages, thus making the
glucose units of cellulose available as major
metabolic entities for the microbes.

In return, the microbes make volatile fatty

acids available for the host

86
This process also takes place (to a limited
extent) by microbes in the colons of
omnivores and carnivores. Fungi and
protozoa secrete cellulases, and the
digestion of wood by termites depends on
protozoa in their digestive tract.
Cellulose, containing over 50% of the
carbon in plant material, is the most
abundant organic compound on earth.
87
Chitin is a key structural polysaccharide
of invertebrates found, for example, in the
exoskeletons of crustaceans and insects.

It consists of N-acetyl-D-glucosamine units

joined by the same (undigestible) β-1,4
glycosidic linkages found in cellulose.

Thus, chitin is similar to cellulose except

that the C-2 moiety is an acetylated amino
group rather than a hydroxyl group 88
Inulin is a fructose polymer found in tubers
and roots of dahlias, artichokes, and
dandelions.
Since it is hydrolyzable to individual
fructose units, it is properly referred to as a
fructosan.

89
This polysaccharide, unlike plant starch, is
easily soluble in warm water, and has been
used in clinical evaluation of kidney
function.
Inulin is freely filtered by the kidneys, it is
not reabsorbed or secreted by the nephron,
it is not metabolized following injection into
blood, it is nontoxic, and therefore its
clearance from the circulation closely
approximates the glomerular filtration rate
(GFR). 90
Dextrins are substances formed in the
course of hydrolytic breakdown of starch
and glycogen in the digestive tract, by
the action of salivary and pancreatic
amylase.

Limit dextrins are the first formed products

as hydrolysis reaches a certain degree of
branching.
91
 Mucopolysaccharides

These materials provide a thin, viscous, jelly-like coating to

cells. H
CH OH
O
2
O
H
The most abundant form is COO- OH H
O H
hyaluronic acid. CH2OH
H
HO
O NH
C O
H CH3
H O O H
H H OH
(1 4) COO - OH H
O H NH
H O
HO C O
CH2OH H CH3
(1 3) H O O H
H H OH

COO-
OH H Alternating units of
O H NH
O
H
HO
H
C O N-acetylglucosamine and
CH3

H OH
H
D-glucuronic acid.
92
 Structural peptidoglycans
Bacterial cell walls are composed primarily of an unbranched
polymer of alternating units of N-acetylglucosamine and N-
acetylmuramic acid.
CH3
CH2OH CH2OH

H O H O O R= CH
H H
OH H O OR H
O H H O L-Ala

H NH H NH D-Isoglu
C O C O
(Gly)5 L-Lys
CH3 CH3
D-Ala

Peptide crosslinks between the polymer strands

(Gly)5
provide extra strength - varies
crosslink for
based on bacterium. Staphylococcus
aureus
93
 Glycoproteins

Proteins that carry covalently bound carbohydrate

units.

They have many biological functions.

• immunological protection
• cell-cell recognition
• blood clotting
• host-pathogen interaction

94
 Glycoprotein structure

Carbohydrates only account for 1-30% of the total

weight of a glycoprotein.

The most common monosaccharides are

glucose mannose
galactose fucose
sialic acid
N-acetylgalactosamine
N-acetylglucosamine

95
 Glycoprotein structure
Linking sugars to proteins. threonine

O-glycosidic bonds using CH2OH CH3

hydroxyl groups of serine andO O O C

H
C
H
threonine OH H

polypeptide chain
H H

H NHCOCH3

N-glycosidic bonds using side

chain amide nitrogen of asparagine
CH2OH O
asparagine residue H
H O N C C C
H H2
OH H
O H

H NHCOCH3

96
 Glycosaminoglycans
(mucopolysaccharides)
Consist or characterized by their content of
amino sugars and uronic acids. When these
chains are attached to a protein, the
compound is known as a proteoglycan.

The amount of carbohydrate in a

proteoglycan is usually much greater than
that found in a glycoprotein, and may
comprise up to 95% of its weight.
97
As ground substance, proteoglycans are
associated with structural elements of
tissues such as bone, elastin, and collagen.
Their property of holding large quantities of
water and occupying space, thus
cushioning or lubricating other structures,
is assisted by the large number of negatively
charged groups on their molecules, which, by
repulsion, keep the carbohydrate chains apart.
Examples are hyaluronate, chondroitin sulfate,
keratan sulfate, and heparin.
98
Keratan sulfate, hyaluronate, and
chondroitin sulfate are found in the
extracellular matrix of cartilage, where they
assist in helping it to cushion compressive
forces.

Hyaluronate is also found in synovial fluid,

the vitreous body of the eye, and in
bacteria.
99
Heparan sulfate, which lacks the
anticoagulant properties of heparin, has
fewer N- and O-sulfated groups yet more N-
acetyl groups than heparin, and is found on
many outer cell surfaces as a proteoglycan.

100
Heparan sulfate is negatively charged, and
participates in cell growth and cell-cell
communication.
It is also found in the basement membrane
of the glomerulus, where it plays a major
role in determining the charge
selectiveness of the renal glomerular
filtration barrier.

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