Monosaccharides

Disaccharides
Polysaccharides (homo-)
Polysaccharides (hetero-)

1
 Photosynthesis and Respiration

Photosynthesis in plants
requires CO2, H2O, and
energy from the sun and
produces carbohydrates,
such as glucose [C6H12O6
hydrate of
=C(H2O)6]. carbon

In respiration, glucose is
oxidized in living cells to
produce CO2, H2O, and
energy.

2
Functions of Carbohydrates

1. Energy source for plants and animals

2. Source of carbon in metabolic processes

3. Storage form of energy
4. Structural elements of cells and tissues

3
1. polyhydroxy ketone C O

-OH > 1

O
2. polyhydroxy aldehyde C H
-OH > 1

3. a larger molecule which can be hydrolyzed

to a polyhydroxy aldehyde or ketone.
4
5
 CHIRAL CENTER / CHIRAL CARBON CH2OH
Ketoseby
Classified and
: Aldose C O
HO C H
1.1.polyhydroxy
Configuration of ketone
chiral carbonC O
farthest
1CHO from 1the
CHO
carbonyl group 2 H2 C OH
HO C H H C OH
KETOSE -OH
3 > 1 H3 C OH
H C OH HO C H
2. Aldose or ketose 4
H C OH HO 4CCHH2OH
5
CH2OH 5 CHCHO
2OH
3. Number of carbons in chain H C OH
O
2. polyhydroxy aldehyde C H HO C H
ALDOSE D-Arabinose
-OH > 1
H C OH
L-Arabinose
6 H C OH
Aldopentose
1CHO 1 CHO 1 CHO 1CHO 1CHO
2 2 2 2 2
H C OH H C H HO C H H C OH HO C H
3
H C OH H 3C OH 3
H C OH HO
3
C H HO C
3
H
4 4 4
H C OH H C OH H 4 C OH H C OH H 4C OH
5 CH2OH 5 CH2OH 5 CH2OH
5 CH2OH 5 CH2OH

D-Ribose D-2-deoksiribose D-Arabinose D-Xilose D-Liksose

Xylose : wood sugar. Xylose is found in the embryo of most

edible plants.
Arabinose is found in nature as a component of biopolymers
such as hemicellulose and pectin and can be metabolised by
microorganisms as a carbon source
7
 Aldohexose 1 CHO
1CHO 1 CHO
2 2 2
H C OH HO C H H C OH
3 3
HO C H HO 3C H HO C H
4 4 4
H C OH H C OH HO C H
H 5C OH 5
H C OH H 5C OH
6 CH2OH 6 CH2OH 6 CH2OH

D-Glucose D-Manose D-Galactose

Mannosa :prevent the adhesion of bacteria to tissues

of the urinary tract and bladder.

source of energy and metabolic intermediate.

one of the main products of photosynthesis and
starts cellular respiration in both prokaryotes
and eukaryotes. 8
 CONCEPTS OF ISOMERS
Two or more different compounds which contain the same
number and types of atoms and the same molecular weights

C5H11OH

CH3-CH2-CH2-CH2-CH3
CH3-CH2-CH2-CH2-CH2-OH
OH
CH3
CH3-CH2 - C -CH3
CH3
OH
CH3-CH -CH2-CH3

OH CH3-CH2-CH2-CH2-CH3

OH 9
 CONCEPTS OF ISOMERS
Stereochemistry
Two or more different compounds which contain the same
Study
number of arrangement
and types ofsame
of atoms and the atoms in 3Dweights
molecular space

Stereoisomer :
C5H11OH

CH3-CH2-CH2-CH2-CH3
1.CH Enantiomer
3 -CH -CH -CH -CH -OH
2 2 2 2
OH
2. Diastereoisomer CH3

3. Epimer
CH
CH3-CH2 - C -CH3
3
OH
4. Anomer
CH -CH -CH:-CH
3
epimer at C - 1
2 3

OH CH3-CH2-CH2-CH2-CH3

OH
10
Enantiomers :
identical chemical and physical properties
differ in their ability to rotate plane - polarized light by
equal amounts but in opposite directions.
differ in crystal shape

A mixture of equal parts of an optically active isomer and its

enantiomer is termed racemic and has a net rotation of plane-
polarized light of zero.

Thalidomide is an example of a racemic drug, in which one

enantiomer produces a desirable effect, whereas the other is
toxic .
11
12
13
D-Glucose is:

found in fruits, corn syrup, and honey.

an aldohexose sugar.
known as blood sugar in the body.
the most abundant organic compound found in
nature 1 C HO
2
H C OH
3
HO C H
4
H C OH
5
H C OH

6 C H2O H
14
Blood Glucose Level

In the body, glucose has a normal

concentration of 70-90 mg/dL.
In a glucose tolerance test, blood glucose is
measured for several hours after ingesting
glucose.

15
 Structural representation
of sugars
Fisher projection:
straight chain representation

Haworth projection: OH H

simple ring in perspective OH

OH

Conformational representation: chair

and boat configurations
16
 Rules for drawing Haworth
projections
if the substituent is to the right in the Fisher
projection, it will be drawn down in the
Haworth projection (Down-Right Rule)

for D-sugars the highest numbered carbon

(furthest from the carbonyl) is drawn up. For
L-sugars, it is drawn down

for D-sugars, the OH group at the anomeric

position is drawn down for and up for .
For L-sugars is up and is down17
 OH H

Fischer projection Haworth projection

OH
for
if the
D-sugars
substituent
the highest
is to thenumbered
right in the OH
carbon (furthest from
the
Fisher
carbonyl)
projection,
is drawn
it will
up.beFor
drawn
L-sugars,
down it is drawn down
-H in the Haworth projection (Down-Right
H O
+ Rule) 6CH2OH
1 C cyclization
5C O
2
H C OH H H
H
3 4C 1C
HO C H for D-sugars, the OH OH H OH
4
H C OH O group at the anomeric OH 3 2
C C
5 position is drawn down
H C O H for and up for . For L- H OH
6 C H2O H sugars is up and is
down
D-Glucose - D - Glucopyranose

Hemiacetal cyclic
( Haworth projection)

18
Chair conformation
 OH H O HO H
H
C1 C1 C1
H C OH H C2 OH H C OH
HO C H HO C3 H HO C H
H C OH O H C4 OH H C OH O
H C5 H C5 OH H C5
CH2OH C6H2OH CH2OH
D-glucose
OH lactol = OH
Anomeric carbon
glycosidic
OH
REDUCING SUGAR
-D-glucopyranose -D-glucopyranose

OH

19
Chair conformation
H
Chair conformation
 MUTAROTATION
OH O HO H
H H
C C C
H C OH H C OH H C OH
HO C H HO C H HO C H
H C OH O H C OH H C OH O
H C H C OH H C
CH2OH CH2OH CH2OH
[ ] + 52.50

crystallize below 980C crystallize above 98 0C

-D-Glucopyranose -D-Glucopyranose

20
Cyclization of D-fructose

-D-fructofuranose
=

-D-fructofuranose

21
 found in dairy products,
in sugar beets
and other gums and
mucilages.
forms part of glycolipids
and glycoproteins in
several tissues.
a nutritive sweetener
because it has food
-D-galactopyranose energy.

22
-D-galactopyranose
 Simplest Carbohydrate - Quiz
Name? Dihydroxy
CH2OH
Acetone
C=O
CH2OH

Is this a polyhydroxy aldehyde? NO

Is this a polyhydroxy ketone? YES
Is this a carbohydrate? YES
Is this a D sugar? NO
Is this an L sugar? NO
Why? center in the molecule
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 Anatomy of a Monosaccharide

Reducing
Primary
group
Reducing alcohol
group
1 CHO 1 CH2OH
2 C D orientation
2 C=O
3 C OH 3 C OH
4 CH2OH 4 CH2OH
Primary
alcohol Primary
alcohol

Aldose Ketose
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PLANE POLARIZED LIGHT

25
26
 OH H O HO H
H
C1 C1 C1
Monosa 1 H Monosa
C OH 2 H C2 OH H C OH
C HO C C H 1. C- OH
HO Cglycosidic
3 H vs HO
C - OH
C Halcohol

OH
H C OH O
OH H C4 monosa
OH 1 H C OH O
H C5 monosa 2
H C5 OH H C5
CH2OH C6H2OH CH2OH
C OC
D-glucose
-1,4 glucosidic
6 CH2OH 6 CH2OH OH lactol = OH
5 O 5 O -glycodic
H2O 6 CH2OH 6 CH2OH
1 OH 1 5
REDUCING SUGARO
4 5 O
OH Lactol 4 OH 1 4 1
HO 3 2OH -D-glucopyranose
H O 3 2 OH Lactol 4 -D-glucopyranose
OH OH
HO O free
OH OH 3 2 3 2 OH lactol
-D-Glucopyranose -D-Glucopyranose OH OH
-D-Glucopyranose -D-Glucopyranose

4-o-( -D-Glucopyranosyl)- -D-Glucopyranose

OH
Maltose
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REDUCING SUGAR. WHY H?
Chair conformation
Chair conformation
Lactose

Lactose is:
Also called milk
sugar.
Composed of
galactose and
glucose linked
by a -1,4-
glycosidic bond.
28
4-O-( -D-galactopyranosyl)-D-glucopyranose
 2. C- OH glycosidic vs C - OH glycosidic
monosa 1
monosa 2

COC
-D-Glucopyranose
6 CH2OH -D-Glucopyranose
5 O 6 CH2OH
1 5 O
4 OH
Lactol -D-Glucopyranosyl- -D-fructofuranoside
HO 4 OH
1 or
3 2 OH
HO -D-Fructofuranosyl - -D-Glucopyranoside
OH 3 2
- H2O OH
6
HOCH2 O H Lactol
O 6 O Sucrose/saccarose
5 2 HOCH2 O
HO Glucose + fructose sucrose
CH2 OH 5 2
4 3 1 HO
OH CH2 OH
4 3 1
-D-Fructofuranose NON REDUCING SUDAR. WHY ?
OH
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-D-Fructofuranose
Sucrose
> also known as tablet sugar
> commercially obtained from sugar
cane or sugar beet
>hydrolysis yield glucose and fructose
invert sugar(invert sugar) Sugar cane
H2O,H+ D-glucose + D fructose
Sucrose ( + 52,50) ( -92,40 )
Hydrolysis
+ 66,50 INVERT - 39 ,70

> used pharmaceutically to make

syrups, troches

Sugar beet 30
 Cellobiose
Two glucose units linked 1-4.
Disaccharide of cellulose.
A mutarotating, reducing sugar.

31
=>
 Gentiobiose
Two glucose units linked 1-6.
Rare for disaccharides, but commonly
seen as branch point in carbohydrates.

=>
32
 monosaccharide condensation polimer

white solid
less water soluble
not sweet

non aldose / ketose

monosacch + monosacch + monosacch + monosaccs

.
O O.
OH OH OH OH OH O OH
OH OH

3 H 2O 33
Exp ; polysaccharide from glucose monomer
linked glikosidic (1,4)

OH lactol OH lactol

O O O O O
1 4 1 4 1 4 1 4
O O O O O O

Simple molecular structure CH2OH

O

O O
OH lactol n OH alcohol

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I. Function
1. Structural Polysaccharide
exp : selulose, chitin dan pectin

2. Nutrition Polysaccharide
exp : amylum, glycogen, inulin

3. Others
polysaccharide attached to others.
exp : Heparin, hialuronic acid

35
II. Hydrolysis
1. Homopolysaccharide
produces one kind of monosacch on
hydrolysis

glucosan glucose
fructosan fructose
galactan galactose
araban arabinose
pentosan pentose
heksosan heksose

2. Heteropolysaccharide
produces other substances on hydrolysis
36
 OH OH

1. Starch
O O OH O
O OH
OH OH OH

The glycosidic bonds in starch O are a-1,4 linkages.

OH
OH O
OH O

It turns out that there are different O kinds O H of starch, one

OH

OH
OH OH
is amylose and another is amylopectin. Plants convert the
O O
OH OH O
OH
O
glucose into O H-1,4 AMYLOSE
starch O
CH O H OH OH
-O1,6 glucosidic
2
O O
O AMYLOSE AMYLOPECTIN O H
O OH
OH
4 1 OH O
OH
OH
1
O
OH
O linkage
OH branchOH
point
O O OH
O O O O
OH OH
OH
OH n OH
O OH

* unbranched (spiral) * branched

OH OH
OH
6 CH 2 O O
OH
OH OH OH OH O
OH
O O O O
H
*300 400O glucose O * 3000 glucose O H O
OH OH O
OH OH
OO OO H
glycosidic (1,4) glycosidic O (1,4).O H branch : (1,6
O H OH
O O
OH OOHH OH
OH OH O
OH O OH

*with I2 deep blue n

*O with I2 purplish redCH O Hn
OH O
O 2
OH OH
OH
O
OH OH
OH O

amylase breaks (1,4)

Amylopectin O .but notO (1,6)
OH
OH
OOH37
OO H O
OH
2. Glycogen
Glucose polymer,similar
to amylopectin a-1,4
linkages and a-1,6
linkages, but even more
highly branched.

Energy storage in
muscle tissue and liver.

The many branched

ends provide a quick
means of putting
glucose into the blood.

picts

38
3. Cellulose
A linear polymer of approximately 2800 D-glucose units
per molecule joined by -1,4- glycosidic bonds

Cellulose is one form of carbohydrate that plants use as

a building material to provide structural strength rather
than for storing glucose for future use

Pict in plant
39
Humans and other animals cannot use
cellulose as food because we lack
-glucosidases, the enzymes that catalyze
the hydrolysis of -glysodic bonds. We
only have -glucosidases, hence are
limited to starch and glycogen with their
-glycosidic bonds.
Many bacteria, however possess
-glucosidases and can digest cellulose.
Animals such as the termite and
ruminants (horses and cows) can digest
cellulose because their digestive systems
contain such bacteria.
40
Agriculture Dept. Announcement
How to identify a mad cow disease ?

normal with mad cow disease

41
Chitin

The major structural component of the exoskeletons

of invertebrates, such as insects and crustaceans;
also occurs in cell walls of algae and fungi
Composed of units of N-acetyl--D-glucosamine joined
by -1,4-glycosidic bonds

42
 Chitin is another example of a structural
carbohydrate. Chitin is found in the exoskeletons
Chitin, a structural polysaccharide
of insects, spiders, and crustaceans. Chitin is also
found in the cell walls of fungi. Chitin is leathery in
pure form but is hardened in most uses via the
deposition of calcium carbonate.
CH2OH
O OH
H
H
OH H
OH H

H NH

C O

CH3

(a) The structure of the (b) Chitin forms the exoskeleton
chitin monomer. of arthropods. This cicada
is molting, shedding its old
exoskeleton and emerging
in adult form.
(c) Chitin is used to make a
strong and flexible surgical
thread that decomposes after
the wound or incision heals.

43