CARBOHYDRATES II

Lecture Contents

the disaccharides
sucrose, maltose, lactose, cellulose

the oligosaccharides
N-linked, O-linked

the polysaccharides
homopolysaccharides
heteropolysaccharides

Objectives

after you have studied this chapter, you should be able to

answer these questions:
what are the general structural features of oligosaccharides
and polysaccharides?
what structural properties of cellulose? what account for its
widespread occurrence in plants?
what are the most common homopolysaccharides and
heteropolysaccharides and what are their functions?
what structural properties distinguish proteoglycans from
glycoproteins?
what are the functions of proteoglycans and glycoproteins?

The Disaccharide

2 monosaccharides joined together to form a glycoside bond

glycosidic bond:
bond bet. one anomeric C of a monosaccharide with a
hydroxyl grp of another monosaccharide
cat. by an enzyme glycosidase via a condensation
reaction
various types: (12); (13); (14) (16) & ,
configurations

crystalline, water soluble, sweet tasting

e.g.: sucrose, lactose, maltose, cellobiose

How is a glycosidic bond formed?

Different types of glycosidic bond

Alpha, where the C1 OH
that is formed ends up
on the same side of the
ring as the -OH of C2

(16)

-linkages
(14)

Beta, where the C1 OH that is formed ends up

on the opposite side of the ring from the -OH of C2

(13)
(12)
(11)

-linkage

Common disaccharides:

sucrose

lactose

maltose

cellobiose

also known as table sugar

extracted from sugar cane,

sugar beet

made up of glucose and

fructose with (12)
glycosidic bond

a nonreducing sugar

common sweetener less

sweet than fructose

-D-glucopyranosyl (12) -Dfructofuranoside

hydrolysis by
sucrase/invertase

also known as milk sugar

-makes up around 2-8% of
the solids in milk

made up of galactose and

glucose with (14)
glycosidic bond

hydrolysis by lactase
(lacking this enzyme can
cause lactose intolerance)

-D-galactopyranosyl (14) -Dglucopyranose

a reducing sugar

also known as malt sugar

intermediate product of
starch hydrolysis

present in germinating
grain, in a small proportion
in corn syrup

made up of 2 molecules
of glucose with (14)
glycosidic bond

-D-glucopyranosyl (14) -Dglucopyranose

a reducing sugar

hydrolysis by maltase

a degradation
product of cellulose

made up of 2
molecules of glucose
linked by (14)
glycosidic bond

does not freely exists

in nature

-D-glucopyranosyl (14) -Dglucopyranose

a reducing sugar

The Oligosaccharide
consists of between 2 - 20 monosaccharides
can be found linked to polypeptide/lipid in glycoprotein &
glycolipid
functions:
glycoprotein immune cell recognition, improve stability
of protein folding, sperm-egg interaction
glycolipid - provide energy, markers for cell recognition
2 types of glycans:
N-linked after N-glycosylation at Asn
O-linked after O-glycosylation at hydroxylysine,
hydroxyproline, Ser or Thr

Oligosaccharides linked to polypeptides forming glycoproteins

oligosaccharides

Asn

Ser

polypeptide
chain

N-linked

O-linked

The diversity of glycoproteins

Carbohydrat
e part

Lipid part

The Polysaccharide

store energy or as structural components

homopolysaccharide
formed from one type of monosaccharide
e.g.: starch, glycogen, cellulose, chitin

heteropolysaccharide
formed from 2/more types of
monosaccharide
e.g.: glycosaminoglycan, peptidoglycan

Homopolysaccharide

Starch

main food storage for plants

consists of:
-amylose linear glucose polymer linked by
(14) bonds
amylopectin glucose units are linked in a linear
way with (14) bonds; branching takes place
with (16) bonds occurring each 24 to 30 glucose
units
degradation enzymes:
amylases
-glucosidase
starch phosphorylase
debranching enzyme

Amylose of starch

(a) The D-glucose residues of amylose linked through

(14) glycosidic bonds
(b) The amylose polymer forms a left-handed helix

Homopolysaccharide

Glycogen
main animal food storage
basic structure similar to amylopectin
but more branches, every 8-12 glucose
residues
more compact
degradation:
amylases
glycogen phosphorylase
glycogen debranching enzyme

Homopolysaccharide

Cellulose
main component of plant cell wall
linear polymer of glucose 15000 residues
linked by (14) linkage
H-bonded structure form parallel microfibril
strong & water resistant
cross-linked with matrix containing other
polysaccharides & lignin resistant to
pressure
degradation celullase

Homopolysaccharide

Chitin
main component of arthropods
exoskeleton as well as algae/fungi cell wall
similar to cellulose except:
every C2OH grp replaced by acetamide
polymer of N-acetyl-D-glucosamine
bonded by (14) linkage
3 types of microfibril: , ,
degradation: chitinase

Struture of chitin

Comparison between struture of cellulose and

chitin

Heteropolysaccharide

Glycosaminoglycan
or mucopolysaccharide
major structural importance in vertebrate animals
e.g. proteoglycan in connective tissues, skin
polymers of repeating disaccharide units (i.e. Nacetylgalactosamine or N-acetylglucosamine or
one of their derivatives) with either sulfate or
carboxylate grps
5 main classes: hyaluronic acid, chondroitin
sulfate, dermatan sulfate, heparin/heparan sulfate
& keratan sulfate

Heteropolysaccharide

Peptidoglycan
cross-linked complex of polysaccharides and peptides found in the cell
walls of bacteria
protects bacteria from osmotic lysis
framework:

polysaccharide component linear chains of alternating (14)-linked

N-acetylglucosamine (NAG) & N-acetylmuramic acid (NAM)
peptide component D-amino acid containing tetrapeptide forms amide
linkage with NAMs lactic acid residue
neighbouring parallel peptidoglycan chains are covalently cross-linked
thru tetrapeptide side chains

Comparison between gram-(-) and gram-(+) bacteria

peptidoglycan framework
a. The peptidoglycan monomer

The peptidoglycan monomer of a

gram-(-) bacterium: e.g. Escherichia
coli

The peptidoglycan monomer of a

gram-(+) bacterium: e.g.
Staphylococcus aureus

b. The peptidoglycan
structure

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