Carbohydrates

Lesson Learning Outcome

Upon completion of this lecture,
students should be able to:
recognize
and
differentiate
carbohydrates
know the functions of carbohydrates

Sugars: Structure and

Stereochemistry

The general formula of carbohydrates -

CnH2nOn, where n varies from 3 to 8

However

only
the
simple
sugars
(monosaccharides) fit this formula exactly
When a few monosaccharides are linked
together, they form oligosaccharides
When many monosaccharides are linked
together, they form polysaccharides
adds monosaccharide units to a growing
carbohydrate molecule involve the loss of one H2O
for each new link formed

Monosaccharides
The most basic units of biologically important
carbohydrates.
They are the simplest form of sugar and are
usually colorless, water soluble.
Some monosaccharides have asweet taste.
glucose(dextrose),fructose(levulose),gala
ctose
Monosaccharides are the building blocks
of disaccharides such
as sucrose and
polysaccharides(such
ascellulose
andstarch).

Structure
Monosaccharides can either be polyhydroxy
aldehyde (aldose) or polyhydroxy ketone (ketose)

Structure
Monosaccharides are classified by their number of
carbon atoms
Name
triose
tetrose
pentose
hexose
heptose
octose

Formula
C3 H6 O3
C4 H8 O4
C5 H1 0 O5
C6 H1 2 O6
C7 H1 4 O7
C8 H1 6 O8

 There are only two trioses

CHO

CH2 OH

CHOH

C=O

CH2 OH

CH2 OH

Glyceraldehyde
(an aldotriose)

Dihydroxyacetone
(a ketotriose)

aldo- and keto- are often omitted and these

compounds are referred to simply as trioses;
although this designation does not tell the nature
of the carbonyl group, it at least tells the number
of carbons

 Glyceraldehyde (aldose with three C)

contains a chiral carbon and exists as a
pair of enantiomers

Fischer Projections
Fischer projection: a two dimensional
representation for showing the configuration of
tetrahedral stereocenters.
horizontal lines represent bonds projecting forward
vertical lines represent bonds projecting to the
rear
the carbon atom at the intersection of the
horizontal and vertical lines is not shown

CHO
H

OH

CH2 OH
D-Glyceraldehyde

convert to
a Fischer
projection

CHO
H

OH
CH2 OH

D-Glyceraldehyde

D,L Monosaccharides
According to the
conventions proposed
by Fischer

D-monosaccharide:a
monosaccharide that,
when written as a Fischer
projection, has the -OH on
the right of the highestnumbered chiral carbon
L-monosaccharide: a
monosaccharide that,
when written as a Fischer
projection, has the -OH on
the left of the highestnumbered chiral carbon

The four aldotetroses

Enantiomers: stereoisomers
are mirror images

that

example: D-erythrose and L-erythrose

Diastereomers: stereoisomers that

are not mirror images
example: D-erythrose and D-threose
Mirror
plane

Mirror
plane

CHO
H
OH
H
OH
CH2 OH

CHO
HO
H
HO
H
CH2 OH

CHO
HO
H
H
OH
CH2 OH

CHO
H
OH
HO
H
CH2 OH

D-Erythrose

L-Erythrose

D-Threose

L-Threose

D,L Monosaccharides
Following are the two most common
D-aldotetroses and the two most
common D-aldopentoses
CHO
CHO
H
OH
HO
H
H
OH
H
OH
CH2 OH
CH2 OH
D-Erythrose

D-Threose

CHO
H
OH
H
OH
H
OH
CH2 OH

CHO
H
H
H
OH
H
OH
CH2 OH

D-Ribose

2-Deoxy-Dribose

What if sugar form cyclic

molecule?
Sugars especially with five or six
carbon atoms normally exist as
cyclic molecule
This is due to interaction between the
functional groups on distant carbons
e.g. C-1 and C-5 to form hemiacetal

What if sugar form cyclic

molecule?

Cyclic sugar can take either of two

different forms ( or ) and are called
anomers of each other

 Free carbonyl (C=O) group can readily form

either - or -anomer
Anomers can be converted from one form to
another through the free carbonyl species

 Fischer projection formulas do not

give a realistic picture of the bonding
situation in the cyclic forms
Thus Haworth projection formulas are
more useful for this purpose.
five and six-membered hemiacetals are
represented as planar pentagons or
hexagons, as the case may be, viewed
through the edge
most commonly written with the
anomeric carbon on the right and the
hemiacetal oxygen to the back right

Haworth Projections
CH=O
CH2 OH
H
OH
OH
H5
O
HO
H redraw
H
OH H C
H
OH
HO
H
5
H
OH
H OH
CH2 OH
D-Glucose
CH OH

anomeric
carbon

O OH()
H5
H
OH H
HO
H

CH2 OH
O
H5
H
H
+
OH H
HO
OH()

H OH
-D-Glucopyranose
(-D-Glucose)

H OH
-D-Glucopyranose
(-D-Glucose)

Haworth Projections
a six-membered hemiacetal ring is shown
by the infix -pyran
a five-membered hemiacetal ring is
shown by the infix -furan

O
Furan

O
Pyran

Conformational Formulas
five-membered rings are so close to
being planar that Haworth projections are
adequate to represent furanoses
HOCH2
H

OH()
H

H
H
HO
OH
-D-Ribofuranose
(-D-Ribose)

HOCH2
H
O
H
H
H
OH()
HO
OH
-D-Ribofuranose
(-D-Ribose)

Conformational Formulas
for pyranoses, the six-membered ring is
more accurately represented as a strainfree chair conformation
HO
HO

CH2 OH
O
OH

OH()

-D-Glucopyranose
(chair conformation)

Conformational Formulas
if you compare the orientations of groups
on carbons 1, 2, 3, 4, and 5 in the Haworth
and
chair
projections
of
-Dglucopyranose, you will see that in each
case
they
are
up-down-up-down-up
respectively
CH2 OH
5

H
4

HO

O OH()

H
OH H

H OH
-D-Glucopyranose
(Haworth projection)

CH2 OH
5
O

HO
HO
3

OH

OH()

-D-Glucopyranose
(chair conformation)

Ascorbic Acid (Vitamin C)

L-Ascorbic acid (vitamin C) is synthesized
both biochemically and industrially from Dglucose
H
HO
H
H

CHO
both biochemial
OH
and industrial
H
syntheses
OH
OH
CH2 OH

D-Glucose

CH2 OH
H
OH O
H
HO
OH
L-Ascorbic acid
(Vitamin C)

Ascorbic Acid (Vitamin C)

L-Ascorbic acid is very easily oxidized to Ldehydroascorbic acid
both are physiologically active and are
found in most body fluids
CH2 OH
H

CH2 OH

OH O
H
HO

O
OH

L-Ascorbic acid
(Vitamin C)

oxidation
reduction

OH O
H

O
O

L-Dehydroascorbic acid

Reactions of monosaccharide
Oxidation and reduction reactions of sugars
play an important role in biochemistry
Oxidation of sugars energy for organisms to
carry out life processes
Highest yield of energy from complete
oxidation of sugar to CO2 and H2O in aerobic
process
The reverse of this reaction takes place in
photosynthesis where sugar is formed as end
product

Oxidation
Reducing sugar: one that reduces
an oxidizing agent
oxidation of a cyclic hemiacetal form
gives a lactone
when the oxidizing agent is Tollens
solution, silver (Ag) precipitates as a
silver mirror
CH2 OH
CH OH
2

H
HO

OH

H
OH H

OH

H OH
A cyclic
hemiacetal

H
+ Ag(NH3 ) 2 +

OHHO

O
H
OH H

O + Ag

H OH
A lactone
(a cyclic ester)

Disaccharides
Sucrose
table sugar; obtained from the juice of
sugar cane and sugar beet
one unit of D-glucose and one unit of
D-fructose joined by an a-1,2-glycosidic
bond CH2 OH
CH2 OH
D-Glucose

HO

OH

HOCH2
D-Fructose

HO
HO
-1,2-glycosidic
bond
HOCH

OH
O
O
HO 2
CH2 OH

OH

OH
O
HO

O
2

CH2 OH

OH

Disaccharides
Lactose
about 5% - 8% in human milk, 4% - 5% in
cows milk
one unit of D-galactose and one unit of Dglucose joined by a b-1,4-glycosidic bond
D-glucose
D-galactose

CH2 OH
O OH

CH2 OH
OH
HO
O O
OH

HO

OH

-1,4-glycosidic bond
HO CH OH
2
O
HO

-1,4-glycosidic bond

O
OH HO

CH2 OH

O
OH

OH

Disaccharides
Maltose
two units of D-glucose joined by an a-1,4glycosidic bond
-1,4-glycosidic bond
HOCH2 O
HO
OH

CH2 OH

OH

OH
HO

OH

HO
HO

CH2 OH
O
1

OH 4 CH2 OH
O
O
OH
HO
OH

Common disaccharides
Disaccharide

Unit 1

Unit 2

Bond

Sucrose(table
sugar,cane
sugar,beet
sugar,
orsaccharose)

Glucose

Fructose

(12)

Lactulose

Galactos
Fructose
e

(14)

Lactose(milk
sugar)

Galactos
Glucose
e

(14)

Maltose
Trehalose
Cellobiose

Glucose
Glucose
Glucose

(14)
(11)
(14)

Glucose
Glucose
Glucose

Structural and
Functions of
Polysaccharides

Polysaccharides
Cellulose: the major structural component
of plants, especially wood and plant fibers
a linear polymer of approximately 2800
D-glucose units per molecule joined by 1,4-glycosidic bonds
fully
extended
conformation
with
alternating 180flips of glucose units
extensive intra- and intermolecular
hydrogen
bonding between
chains
HO-CH2
HO-CH
OH
4

O
HO

OH

HO
O 4

HO-CH2

O
HO

OH

Polysaccharides
Starch: is used for energy storage in plants
a polymers of a-D-glucose units
amylose: continuous, unbranched chains of up to
4000 a-D-glucose units joined by -1,4-glycosidic
bonds
amylopectin: a highly branched polymer consisting
of 24-30 units of D-glucose joined by -1,4glycosidic bonds and branches created by -1,6glycosidic bonds

Polysaccharides
Glycogen is a branced-chain polymer of -Dglucose like amylopectin
It also consist of a chain of -1,4-glycosidic
bonds and branches created by -1,6glycosidic bonds
The difference is that glycogen is more
branched than amylopectins

Polysaccharides

Polysaccharides
Chitin: the major structural component of the
exoskeletons of invertebrates, such as insects
and crustaceans; also occurs in cell walls of
algae, fungi, and yeasts
composed
of
units
of
N-acetyl--Dglucosamine joined by -1,4-glycosidic bonds

Polysaccharides
Bacterial cell walls: prokaryotic cell
walls are constructed on the framework of
the repeating unit NAM-NAG joined by 1,4-glycosidic bonds

Plant Cell Walls

consist largely of
cellulose
also contain pectin
which functions as an
intercellular cementing
material
pectin is a polymer of
D-galacturonic acid
joined by -1,4glycosidic bonds
the major
nonpolysaccharide of
cell walls, especially in

woody plants, is
lignin

Polysaccharides
Glycosaminoglycans:
polysaccharides
based on a repeating disaccharide where
one of the monomers is an amino sugar and
the other has a negative charge due to a
sulfate or carboxylate group
heparin: natural anticoagulant
hyaluronic acid: a component of the
vitreous humor of the eye and the
lubricating fluid of joints
chondroitin sulfate and keratan sulfate:
components of connective tissue

Glycoproteins
Glycoproteins contain carbohydrate
units
covalently
bonded
to
a
polypeptide chain
antibodies are glycoproteins
carbohydrates
play
a
role
as
antigenic determinants, the portions
of the antigenic molecule that
antibodies recognize and to which
they bind

Blood Group Substances

Membranes of animal plasma cells have
large
numbers
of
relatively
small
carbohydrates bound to them
these membrane-bound carbohydrates
act as antigenic determinants
among the first antigenic determinants
discovered were the blood group
substances
in the ABO system, individuals are
classified according to four blood types:
A, B, AB, and O

Thanks for your

attention