GLYCOSIDES

Formation of glycosides
Recall that an alcohol can react with a hemiacetal to form an acetal (a di-ether). When an
alcohol reacts with a cyclic hemiacetal of a monosaccharide the cyclic acetal product is called
a glycoside. The new ether bond is called a glycosidic bond. Monosaccharides are linked
together by glycosidic bonds to form disaccharides and polysaccharides. Alkyl glycosides can
not undergo mutarotation, and so are not reducing sugars-D-Glucose Methanol Methyl--D-
glucoside.

DISACCHARIDES

Monosaccharides can form cyclic structures by the reaction of the carbonyl group with an OH
group, resulting in an cyclic hemiacetal (or hemiketal for ketoses). In the same way that
hemiacetals and ketals can react with an additional alcohol forming acetals and ketals, these
cyclic monosaccahrides can in turn react with another alcohol molecule. In the case of
disaccharides, one monosaccharide acts as the hemiacetal while the other
monosaccharides acts as the alcohol. The formation of an acetal (or ketal) bond between
two monosaccharides is called a glycosidic bond or glycosidic linkage. Therefore,
disaccharides are sugars composed of two monosaccharide units that are joined by a carbon–
oxygen-carbon linkage known as a glycosidic linkage. This linkage is formed from the
reaction of the anomeric carbon of one cyclic monosaccharide with the OH group of a second
monosaccharide.
.

The disaccharides differ from one another in their monosaccharide constituents and in the
specific type of glycosidic linkage connecting them. There are three common disaccharides:
maltose, lactose, and sucrose. All three are white crystalline solids at room temperature and
are soluble in water. We’ll consider each sugar in more detail.

Disaccharides can be reducing or non-reducing, depending on the specific groups involved

in the formation of the glycosidic bond. Disaccharides can only be reducing when there is a
free anomeric carbon, not involved in the formation of the glycosidic bond, that can undergo
the oxidation reduction with Tollen's or Benedict's reagents. When the anomeric carbon on
both monosaccharides is involved in the formation of the glycosidic bond, the disaccharides
is non-reducing.

MALTOSE
LACTOSE

FORMATION OF SUCROSE:
Is sucrose a reducing sugar?

Hydrolysis of Sucrose

In the hydrolysis of any di- or poly saccharide, a water molecule helps to break the acetal
bond as shown in red. The acetal bond is broken, the H from the water is added to the oxygen
on the glucose. The -OH is then added to the carbon on the fructose.

Figure 11: Hydrolosis of Sucrose

Non-reducing sugars do not have a free ketone or aldehyde group. These sugars have acetal
in place of hemiacetal. An acetal consists of two O-R group, one -R and -H group
respectively. All these groups are attached to the same carbon.
Sucrose is a non-reducing sugar because
The two monosaccharide units are held together by a glycosidic linkage between C 1 of α-
glucose and C2 of β-fructose. Since the reducing groups of glucose and fructose are involved
in glycosidic bond formation, sucrose is a non-reducing sugar.
 Anomeric carbon of both the monosaccharides are involved in glycoside or acetal
formation. So it does not have a free -CHO group
Examples of non reducing sugars
Stachyose, Sucrose, Verbascose, Trehalose and Raffinose are the five examples of non
reducing sugars. Carbohydrate: A carbohydrate can be defined as a biomolecule that owns the
atoms of hydrogen, oxygen and carbon.
There are two functionally different classes of disaccharides:

Reducing disaccharides, in which one monosaccharide, the reducing sugar of the pair, still
has a free hemiacetal unit that can perform as a reducing aldehyde group: lactose, maltose
and cellobiose are examples of reducing disaccharides, each with one hemiacetal unit, the
other occupied by the glycosidic bond, which prevents it from acting as a reducing agent.

Non-reducing disaccharides, in which the component monosaccharides bond through

an acetal linkage between their anomeric centers. This results in neither monosaccharide
being left with a hemiacetal unit that is free to act as a reducing
agent. Sucrose and trehalose are examples of non-reducing disaccharides because their
glycosidic bond is between their respective hemiacetal carbon atoms. The reduced chemical
reactivity of the non-reducing sugars in comparison to reducing sugars, may be an advantage
where stability in storage is important.