Carbohydrates

Chapter
Chapter 11

DR. LEONARDO C. MEDINA, JR.

1

Chapter Outline
1. Carbohydrates: A First
Class of Biochemicals
2. Classification of
Carbohydrates

4. Monosaccharides
5. Structure of Glucose and
Other Aldoses

3. Importance of
Carbohydrates

Chapter Outline (continued)

6. Cyclic Structure of
Glucose; Mutarotation
7. Hemiacetals and Acetals
8. Structures of Galactose
and Fructose
9. Pentoses
10. Disaccharides

11. Structures and Properties

of Disaccharides
12. Sweeteners and Diet
13. Redox Reactions of
Monosaccharides
14. Polysaccharides Derived
from Glucose

Carbohydrates:
A First Class of
Biochemicals
4

 Carbohydrates are generally defined as

polyhydroxy aldehydes or ketones or
substances that yield these compounds
when hydrolyzed.
H
CHO

OH

OH

H
glyceraldehyde

OH

OH

H
dihydroxyacetone 5

Classification
of
Carbohydrates
6

A carbohydrate can be classified

as:
1.monosaccharide
2.disaccharide
3.oligosaccharide
4.polysaccharide
7

Monosaccharides
A monosaccharide is a carbohydrate that
cannot be hydrolyzed to simpler
carbohydrate units.
The monosaccharide is the basic
carbohydrate unit of cellular metabolism.

Disaccharides
A disaccharide yields two
monosaccharides either alike or
different when hydrolyzed:
H+ or

disaccharide + water 2 monosaccharides

enzymes

Monosaccharides & Disaccharides

Disaccharides are often used by plants or
animals to transport monosaccharides from
one cell to another.
The monosaccharides and disaccharides
generally have the ending ose for example,
glucose, sucrose, and lactose.
These are water-soluble carbohydrates, which
have a characteristically sweet taste and are
called sugars.
10

Oligosaccharides
An oligosaccharide has two to six
monosaccharide units linked together.

11

Polysaccharides
A polysaccharide is a macromolecular substance
that can be hydrolyzed to yield many
monosaccharide units:
H+ or

polysaccharide + water monosaccharides

enzymes

Polysaccharides are important structural

supports, particularly in plants, and also serve
as a storage depot for monosaccharides, which
cells use for energy.
12

Other Ways to Classify Carbohydrates

As a triose, tetrose, pentose, hexose, or
heptose
As an aldose or ketose
As a D or L isomer
As a (+) or (-) isomer
As a furanose or a pyranose
As having an alpha () or beta ()
configuration
13

Importance of
Carbohydrates
14

Importance of Carbohydrates
1. Carbohydrates are very effective
energy-yielding nutrients.
2. Carbohydrates can serve as very
effective building materials.
3. Carbohydrates are important watersoluble molecules.
15

Monosaccharides

16

Monosaccharides
The hexose monosaccharides are the most
important carbohydrate sources of cellular
energy.
Three hexoses glucose, galactose, and
fructose are of major significance in
nutrition.
All three have the same formula, C6H12O6, and
thus deliver the same amount of cellular energy.
They differ in structure, but are biologically
interconvertible.
17

 Glucose (dextrose) is the most important of

the monosaccharides.
It is an aldohexose and is found in the free
state in plant and animal tissue.
CHO
H
HO

OH
H

OH

OH
CH2OH

18

 Galactose is also an aldohexose and

occurs, along with glucose, in lactose and
in many oligo- and polysaccharides such
as pectin and gums.
CHO
H

OH

HO

HO

OH
CH2OH

19

 Fructose, also know as levulose, is a ketohexose

that occurs in fruit juices, honey, and along
with glucose, as a constituent of sucrose.
CH2OH
O
HO

OH

OH
CH2OH

20

Structures of Glucose
and Other Aldoses

21

Epimers
Any two monosaccharides that differ
only in the configuration around a
single carbon atom are called epimers.
D- and L-glyceraldehyde are epimers.
CHO

CHO
H

OH

HO

CH2OH

CH2OH

D-glyceraldehyde

L-glyceraldehyde

22

Configurations of the D-family of aldoses. The

hydroxyl group on the new chiral carbon atom,
added in going from triose to tetrose to pentose to
hexose, is shown in red.
23

Configurations of the D-family of aldoses.

The hydroxyl group on the new chiral carbon
atom, added in going from triose to tetrose to
pentose to hexose, is shown in red.
24

Configurations of the D-family of aldoses. The

hydroxyl group on the new chiral carbon atom,
added in going from triose to tetrose to pentose to
hexose, is shown in red.
25

An example of the Kilani-Fischer synthesis in which two

aldotetrose molecules are formed from an aldotriose
molecule.
26

Cyclic Structure of
Glucose; Mutarotation
27

Mutarotation
of D-glucose

28

Anomers

When two cyclic isomers differ only

in their stereo arrangement about the
carbon involved in mutarotation, they
are called anomers.

Mutarotation is the process by

which anomers are interconverted.
29

Three-dimensional representations of the chair form

of -D-glucopyranose
30

Hemiacetals and
Acetals
31

 Cyclic structures of monosaccharides are

intramolecular hemiacetals.
Five- or six-membered rings are especially
stable.
CH2OH
O

hemiacetal structure
in -D-glucopyranose

OH
HO

HO
HO

32

Glycoside
When a monosaccharide hemiacetal reacts with
an alcohol, the product is an acetal.
In carbohydrate terminology, this acetal
structure is called a glycoside.
CH2OH

acetal structure

O
OH
HO

RO
HO

glycosidic linkage
33

Structures of Galactose
and Fructose
34

Galactose
CHO
H
HO

CH2OH

CH2OH
OH

OH

OH

OH
HO
H

O OH
OH

H
OH
CH2OH

D-galactose

HO
OH
-D-galactopyranose

HO
-D-galactopyranose

35

Fructose
CH2OH
O
CH2OH
HO

OH

OH

OH

OH

CH2OH

CH2OH
OH

36

Disaccharides
37

Disaccharides
Disaccharides are carbohydrates composed
of two monosaccharide residues united by a
glycosidic linkage.
or
sucrose + water H+

glucose
+
fructose
sucrase
lactose + water
galactose
+
glucose
lactase
H+ or

maltose + water H+
or glucose + glucose
maltase
38

Structures and
Properties of
Disaccharides
39

 Disaccharides contain an acetal

structure (glycosidic linkage), and
some also contain a hemiacetal
CH2OH
CH2OH
structure.
Maltose:
O
O
OH

HO
O

OH
OH

HO
HO

-1,4-glycosidic linkage

40

Sweeteners
Sweeteners
and Diet
41

42

Redox Reactions of
Monosaccharides
43

Oxidation
The aldehyde groups in monosaccharides can
be oxidized to monocarboxylic acids by mild
oxidizing agents such as bromine water.
CHO
H
HO

COOH
OH

HO

OH
H

+ Br2 + H2O

+ 2HBr

OH

OH

OH

OH
44

CH2OH

CH2OH

Reduction
Monosaccharides can be reduced to their
corresponding polyhydroxy alcohols by
reducing agents such as H2/Pt or sodium
amalgam, Na(Hg).
CHO
H
HO

CH2OH
OH

HO

OH
H

+ H2 / Pt
H

OH

OH

OH

OH

CH2OH

CH2OH

45

Redox Test for Carbohydrates

Under prescribed conditions, some
sugars reduce silver ions to free silver,
and copper (II) ions to copper (I) ions.
Such sugars are called reducing
sugars.
46

Polysaccharides
Derived from
Glucose
47

Starch
Starch is found in plants, mainly in the seeds,
roots, or tubers.
Corn, wheat potatoes, rice and cassava are the
chief sources of dietary starch.
The two main components of starch are
amylose and amylopectin.
Amylose molecules are unbranched chains
composed of about 25-1300 -D-glucose units
joined by -1,4-glycosidic linkages.
48

Representation of amylose.
49

50

51

Glycogen
Glycogen is the energy-storage carbohydrate of
the animal kingdom.
It is formed by the polymerization of glucose
and is stored in the liver and in muscle tissues.
Structurally, it is very similar to the
amylopectin fraction of starch, except that it is
more highly branched.
The -1,6-glycosidic linkages occur on one of
every 12-18 glucose units.
52

Cellulose
Cellulose is the most abundant organic
substance found in nature.
It is the chief structural component of
plants and wood.

53

Two representations of
cellulose. In the threedimensional drawing,
note the hydrogen
bonding that links the
extended cellulose
polymers to form
cellulose fibers.
54

55