REACTION OF

MONOSACCHARIDES
1. Siti Agustiyaningsih 15030194027
2. Utari Ika Cahyani 15030194035
3. Diyah Amalia Putri 15030194075

PKU-15
OXIDATION
REACTION
Aldonic Acid
Aldonic acid is an aldose is easily oxidized to yield
the corresponding carboxylic acid.
A buffered solution of aqueous Br2 is better oxidant

pH 5-6
Aldaric Acid
When diluted of HNO3 which is powerful oxidizing
agent is used, an aldose is oxidized to a
dicarboxylic acid.

HNO3
Heat
Uronic Acid
If only the –CH2OH end of the aldose is oxidized without affecting the –
CHO group, the product is a monocarboxylic acid called a uronic acid
H
O
HC
2 H
OC
2
O O O
H
O O
H H
O O
H
HO enzime
HO
O
H O
H
C H O
C H O
H O H
H O H

H O H H O H
O
H O H enzime H O H

H O H H O H

C H 2 O H C O 2 H

D-Glucose D-Glucuronic acid

 Periodate Acid
a compound which is 1,2 diol or α-hydroxy of aldehydes or ketones are oxidized and
forced separation by periodate acid (HIO4) .

O
O
H
O
H O

+ HIO3
H
I
O
4 +
R
H
C
C
H
R
R CH HC R

1,2-diol

B ein g -C O 2 H B e in g -C H O
O O

O OH H
I
O
4
R COH + HC R + HIO3

RC CHR
α-hydroxy of aldehydes or ketones
REDUCTION
REACTION
 Reduction Of Monosaccharides

H2O

ß-D-Glucopyranose
D-Glucose D-Glucitol
(D-Sorbitol),
an alditol
Monosacharaides can further be classified into
aldose & ketose. If the monosaccharide contain
an aldehyde group (-CHO), it is known as aldose.
E.g., glucose.
Monosacharides which contains a ketone group
(>C=O) then it is known as ketoses. E.g.,fructose.
ESTER-ETER
REACTION
 Acetate Ester Formation
Esterification is normally carried out by treating the carbohydrate with an
acid chloride or acid anhydrate in the presence of a base.

◦ Acetic anhydride with pyridine catalyst converts all the oxygens to acetate
esters.
◦ Esters are readily crystallized and purified.
GLYCOSIDE
REACTION
 Formation of Glycosides
Treatment of a monosaccharide hemiacetal with an alcohol
and acid catalyst yields an acetal called a glycoside.

◦ React the sugar with alcohol in acid.

◦ Since the open-chain sugar is in equilibrium with its - and -
hemiacetal, both anomers of the acetal are formed.
◦ Aglycone is the term used for the group bonded to the anomeric
carbon.
Aglycones

◦ The group bonded to the anomeric carbon of a

glycoside is called an aglycone.
◦ Some aglycones are bonded through an oxygen
atom (a true acetal), and others are bonded
through other atoms such as nitrogen.
Methyl Ether Formation

◦ Reaction of the sugar with methyl iodide and

silver oxide will convert the hydroxides to methyl
ethers.
◦ The methylated sugar is stable in base.