Biochemistry: A Short Course

Tymoczko • Berg • Stryer
Biochemistry: A Short Course
CHAPTER 10
Carbohydrates
Chapter 10 – Carbohydrates
Most carbohydrates are produced photo-synthetically

by bacteria, algae and plants
Carbohydrates (“hydrate of carbon”) have the empirical formula

of (CH2O)n , where n ≥ 3.
- Monosaccharides: one monomeric unit

- Oligosaccharides: ~2-20 monosaccharides
- Polysaccharides: > 20 monosaccharides
- Glycoconjugates: linkages to proteins or lipids
Monosaccharides of varying length
Aldoses and Ketoses
Trioses – three carbon sugars
Ketotriose Aldotriose
Aldoses and Ketoses
Tetroses – 4 carbon sugars
Chiral designation comes from

the most distant chiral carbon
from the carbonyl
D-monosaccharides dominate
in nature
Aldoses and Ketoses
Pentoses – 5 carbon sugars

Hexoses – 6 carbon sugars
Chiral designation comes from

the most distant chiral carbon
from the carbonyl
Isomeric forms of carbohydrates
Epimers
- Epimers – sugars that differ at

only one of several chiral
centers.
example: D-Mannose is an
epimer of D-Glucose
Cyclization of D-glucose
to form D-glucopyranose
C1 is called the
anomeric carbon
In aqueous solutions hexoses and

pentoses will cyclize, forming alpha
(a) and beta (b) forms
Reducing and Nonreducing ends of sugars
- In linear polymeric chains of monosaccharides there

is usually one reducing end (containing the free anomeric
carbon) and one nonreducing end
- Branched polysaccharides have a number of nonreducing

ends, but only one reducing end
Nonreducing end Reducing end

(anomeric carbon)
Sugars that react with oxidizing agents are called reducing sugars.
As a reducing sugar, glucose can react with hemoglobin, forming
glycosylated hemoglobin (hemoglobin A1c).
Clinical Insight page 185

Cyclization of D-fructose
to form a- and b-fructofuranose
anomeric carbon
In aqueous solutions, it is the ring structures that dominate
These rings are NOT planar
Modified Monosaccharides
6-deoxy-L-galactose
Important in structural
glycans
Important in
metabolic pathways
Disaccharides and other Glycosides
Glycosidic bond – the primary structural linkage in all polymers
of monsaccharides
Glycosides – glucose provides the anomeric carbon
Structures of disaccharides: maltose

More structures of disaccharides: lactose and sucrose
Most abundant sugar

Major carbohydrate
in milk
Sucrase, lactase and

maltase are found
on the outer surface
of the epithelial cells
lining the small
intestine.
Comes from the breakdown of starch and glycogen

Polysaccharides
- Homoglycans – homopolysaccharides containing only one

type of monosaccharide.
- Heteroglycans – heteropolysaccharides containing residues

of more than one type of monosaccharide
- The lengths and compositions of a polysaccharide may vary

within a population of these molecules
examples: starch and glycogen – storage polysaccharides
cellulose and chitin – structural polysaccharides
Starch
- D-glucose is stored intracellularly in polymeric forms
- plants and fungi store glucose as starch
- Animals store glucose as glycogen
- Starch is a mixture of amylose (unbranched)

and amylopectin (branched every 25-30 glucose units)
(a) Amylose is a linear polymer

containing only a-1,4-glycosidic
bonds.
(b) Amylopectin is a branched

polymer also contains a-1,6-bonds
Starch is stored by plants and used as fuel.
Prentice Hall c2002 Chapter 8 18

The Enzyme -Amylase Digests Starch
a-Amylase is a hydrolase enzyme that hydrolyzes

internal a-1,4 glycosidic bonds.
Glycogen is is stored by animals and used as fuel.
Prentice Hall c2002 Chapter 8 20

Glycogen
- Glycogen is the main storage polysaccharide of humans
- Glycogen is a polysaccharide of glucose residues connected

by a-1,4 linkages with a-1,6 branches (one branch every
8 to 12 residues)
- Glycogen is present in large amounts in liver and skeletal muscle

Cellulose – a structural polysaccharide that is a
Major component of cell walls of plants
Cellulose has b-1,4 glycosidic bonds
Each glucose
residue is rotated
180o relative to
the next residue
Extended hydrogen bonding

between chains leads to
bundles or fibrils
Glycosidic bond determines
polysaccharide structure
Straight structure
Bent structure
- Humans digest starch and glycogens ingested in their diet
using amylases, enzymes that hydrolyze a-1,4 glycosidic bond
- Humans cannot hydrolyze b-1,4 linkages of cellulose. Therefore

cellulose is not a fuel source for humans. It is fiber.
- Certain microorganisms have cellulases, enzymes that hydrolyze

b-1,4 linkages of cellulose.
- cattle have these organisms in their rumen

- termites have them in their intestinal tract
Carbohydrates attached to proteins form glycoproteins
Two methods to anchor the protein to carbohydrates
or Thr
Mucins or mucoproteins are

proteins which have the
monosaccharide
N-acetylgalactosamine attached.
This glycoprotein is found in mucus
and is a lubricant.
N-linked oligosaccharides
All N-linkages have a common core shown in grey.
Additional sugars can be attached to these cores to make diverse and unique structures
Complex structure
High mannose
Protein residue Protein residue

Proteoglycans are glycoproteins where the protein is bound to a
special class of polysaccharides called a glycosaminoglycan.
This class of glycoprotein are used as structural components and lubricants.
In proteoglycans nearly 95% of

the mass comes from the
polysaccharide.
Proteoglycans function as
lubricants, structural
components in tissue and
mediate the adhesion of cells to
the extracellular matrix.

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Tymoczko • Berg • Stryer

Biochemistry: A Short Course

Most carbohydrates are produced photo-synthetically

Carbohydrates (“hydrate of carbon”) have the empirical formula

- Monosaccharides: one monomeric unit

Chiral designation comes from

Pentoses – 5 carbon sugars

Chiral designation comes from

- Epimers – sugars that differ at

In aqueous solutions hexoses and

- In linear polymeric chains of monosaccharides there

- Branched polysaccharides have a number of nonreducing

Nonreducing end Reducing end

Clinical Insight page 185

Glycosides – glucose provides the anomeric carbon

Structures of disaccharides: maltose

Most abundant sugar

Sucrase, lactase and

Comes from the breakdown of starch and glycogen

- Homoglycans – homopolysaccharides containing only one

- Heteroglycans – heteropolysaccharides containing residues

- The lengths and compositions of a polysaccharide may vary

- Starch is a mixture of amylose (unbranched)

(a) Amylose is a linear polymer

(b) Amylopectin is a branched

Prentice Hall c2002 Chapter 8 18

a-Amylase is a hydrolase enzyme that hydrolyzes

Prentice Hall c2002 Chapter 8 20

- Glycogen is a polysaccharide of glucose residues connected

- Glycogen is present in large amounts in liver and skeletal muscle

Extended hydrogen bonding

- Humans cannot hydrolyze b-1,4 linkages of cellulose. Therefore

- Certain microorganisms have cellulases, enzymes that hydrolyze

- cattle have these organisms in their rumen

Mucins or mucoproteins are

Protein residue Protein residue

In proteoglycans nearly 95% of

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