An Introduction

W.T. Winter
wtwinter@syr.edu
215 Jahn Lab; x6876

Overview

Monosaccharides?
Oligosaccharides?
Polysaccharides
Glycoproteins and Proteoglycans

Carbohydrates Are Chiral

Molecules

Typically but not always

L amino acids

D - sugars

Hence, these molecules have

a measurable optical
rotation, which depends
upon both the monomer
residues and their
conformation

L
Glyceraldehyde

Fisher Formulas
Next to last
carbon
determines
D or L

New carbon is added as C1

A Way to Explore Monosaccharides

John Maser at Leeds has developed a
Monosaccharide Browser the site is
http://www.beechtreecommon.org/biochem
istry/monosaccharide
/

Epimers Differ by Configuration at

One Chiral Center
D-glucose

C2 epimer

D-mannose

C3 epimer

D-allose

C4 epimer

D-galactose

C5 epimer

L-idose

Sugars Prefer To Be Cyclic

Hemiacetals and Cyclization Group

-D-Glucose
In nature, open chain
forms are rare.
NMR has shown that
all 5 coexist with the
pyranose forms
occurring 99% of the
time, furanose about
0.5% each and a
trace of open chain

and are anomers

and differ in
configuration at the
new chiral center
formed in the cycle

Pyranose Ring Shapes

Pyranose rings can form chair and boat
conformers

C4

C1

Sucrose
1-2 linked alpha
glucose, beta fructose
Sources sugar cane
sugar beet

Polysaccharides
Polysaccharides consist of sugar residues
linked into a polymer.
Polysaccharides, unlike proteins or nucleic
acids, are not always linear in sequence
The most abundant biomolecules in
nature-about 1012 tons of cellulose are
synthesized each year
Functions: structural, food storage, cell
surfaces, extracellular matrices.

Polysaccharides May Be the Most

Diverse Biomolecules
From one 6 carbon
hexopyranose sugar
such as glucose, you
can make 11 different
disaccharides and 8
of those lead to
infinite polymers
From one amino acid or
nucleotide you can
make only a single
dimer.

CH2OH

CH2OH

OH

OH

OH
OH

OH
OH

-D-Glucose

OH
OH

-D-Glucose

Cellulose: Structural
polysaccharide from glucose

n ~ 5000-10000
Also found in some
bacteria, algae, fungi,
seed hairs, and
animals (tunicates or
sea squirts)

Microfibrils
of cellulose

Wood cell (fiber) cell walls

are made of cellulose +
lignin and hemicelluloses

Starch: a-D-Glucose polymer found

as an energy storage material in
foods
Unlike cellulose,
starch can be
metabolized by
humans.
Starches provide
the bulk of the
energy we obtain
from grains,
potatoes etc.

Amylose

Amylopectin

Extracellular Matrix: Hyaluronic acid

A regular copolymer of N-acetyl glucosamine and Glucuronic Acid (as a metal salt)

HA cont
Found in:
synovial fluid (knee, shoulder )
Vitreous humor (eye- used in
reconstructive eye surgery)
Skin small amounts in all connective
tissues

Connective Tissues- fibrous

proteins, polysaccharides, and
proteoglcans

Other Structural Polysaccharides

Mannans some algae
Alginic acids many algae
Chitin- insects, crustaceans (shrimp shell),
fungi.