SOME IMPORTANT MONOSACCHARIDES

A. HEXOSES:
Glucose, fructose, galactose and mannose are described below:

1. D-Glucose:
It is also called grape sugar and dextrose (because of dextrorotation) and occurs as such,
widely distributed in nature (fruits, sugar cane, sugar beats, dates).
Human blood plasma contains 70 to 110 mg glucose/dL in the fasting condition. Under
normal conditions only a trace of glucose passes out in urine which can only be
demonstrated by special methods. However, large amounts of glucose are found in the
urine of patients of diabetes mellitus.
Because glucose represents almost 100% of monosaccharide in the blood, therefore the
term blood sugar is used for blood glucose.
Glucose is the principal monosaccharide utilized by the tissues for obtaining energy.
Glucose is 74% as sweet as sucrose.it exhibits mutarotation. It is readily fermented by
yeast.

2. D-Fructose:
It is also called fruit sugar (Latin fructus fruit) and levulose (due to levorotation) and
occurs in honey and in plant kingdom as such or as combined with glucose in sucrose.
It exhibits mutarotation. When free, it occurs in pyranose form which is levorotatory,
however in sucrose it exists in the furanose form which is dextrorotatory.
The polysaccharide inulin used in investigating kidney function yields it on hydrolysis.
Animal tissues also contain it in small amounts. Seminal fluid has appreciable amounts of
fructose.
Fructose is the sweetest of all sugars (173% of sucrose). It is fermented by yeast.

3. Galactose:
It mainly occurs as a part of the lactose (milk sugar) molecule in which it is combined
with glucose. It also occurs in the seed coats of legumes. It is a constituent of glycolipids
and glycoproteins.
It is an aldohexose, is dextrorotatory and exhibits mutarotation.
It has a 32% sweetness of sucrose. It differs from glucose only in respect to configuration
around carbon No. 4 (epimers).
 D-galactose; straight chain (left) and Haworth's formula (right) showing it as
galactopyranose (1-5 ring).

4. D-Mannose:
It is a part of the molecule of the prosthetic polysaccharide of many glycoproteins.
If ingested, it is absorbed and in the body it is converted to glucose.
It shows chemical reactions similar to glucose, it cannot be differentiated from glucose by
configuration around carbon No.2; in other words it is an epimer of glucose in respect to
carbon No. 2.

B. PENTOSES
Pentoses are monosaccharides containing a chain of five carbon atoms. Ribose is a constituent of
the ribonucleic acid (RNA) of the cell and of many important substances found in cells, such as
ATP, GTP, NAD NADP, FAD and coenzyme A.
Pentoses have the following properties:
1. They may be aldoses or ketones.
2. They possess strong reducing properties
3. They form osazone crystals with phenylhydrazine
4. With acids they are converted to furfurals
5. They are not fermented by yeast
6. Several pentoses have important physiological roles as given below:
● Ribose and ribulose as phosphates are intermediates in the pentose phosphate pathway of
glucose metabolism.
● D-arabinose and D-xylose are found in glycoproteins.
Pentoses are an important constituent of the diet of herbivorous animals, but their role in human
nutrition is not well established.
 Deoxy-D-ribose

DISACCHARIDES

The disaccharides consist of two monosaccharide units joined covalently by an O-glycosidic

linkage. The most common disaccharides are sucrose maltose and lactose

1. Sucrose:
It is also called saccharose and is the common table sugar.
Upon hydrolysis yields 1 molecule of each D glucose and D-fructose. Because sucrose,
unlike maltose and lactose, contains no free anomeric carbon atom (both potential
aldehyde and ketone groups on anomeric carbon are blocked from activity), therefore it is
without reducing properties which appear only when it has been hydrolyzed, yielding its
constituent monosaccharides. For the same reason, sucrose does not form osazone
crystals and also does not show the property of mutarotation.

Sucrose is dextrorotatory because it has in its molecule glucose which is dextrorotatory

and fructose which being in furanose form is also dextrorotatory. When sucrose is
hydrolyzed, its fructose is released in its pyranose form which is levorotatory. On
hydrolysis, sucrose becomes levorotatory. This is because out of glucose and fructose
which result from hydrolysis of sucrose in equal amounts, the levorotatory activity of
fructose is more than dextrorotatory activity of glucose. Because in this process the
 rotation has been reversed, this process is called inversion and the products of sucrose
hydrolysis are called invert sugar.
Honey is very rich in invert sugar because the honey bee has an enzyme invertase which
converts sucrose into invert sugar. Inversion can be brought about by hydrolysis with
dilute acids or with a specific enzyme called invertase or sucrase.
Invert sugar is 30% more sweet than sucrose.
Sucrose, like other disaccharides, can be utilized in the body only if taken by mouth
because the specific intestinal enzyme, sucrase, hydrolyzes it to glucose and fructose
which are then absorbed. If given by an intravenous injection, it is not metabolized and is
rapidly excreted in urine.

2. Maltose:
It is formed by an O-glycosidic linkage (1→4) between one molecule of ⍺-D-glucose
with another molecule of ⍺-D-glucose with the elimination of one water molecule.

Because of the presence of a free anomeric carbon atom, it is a reducing sugar, forms
osazone crystals and shows mutarotation.
It is 32% as sweet as sucrose.
It is formed in vivo by the action of salivary amylase on starch and in vitro by partial
hydrolysis of starch by acids. Further acid hydrolysis of starch or the action of the
enzyme maltase will result in the production of glucose. Maltose is present in various
baby and invalid foods.

Note: Another disaccharide containing two molecules of ⍺-D-glucose is isomaltose, however in

this case the two ⍺-D-glucose molecules have 1-6 linkage.
3. Lactose:
It is also called milk sugar (lac milk).
It is formed as a result of O-glycosidic linkage between one molecule of β-D-galactose
and I molecule of D-glucose through β1→4 linkage.

In nature it occurs exclusively in milk. The enzyme lactase present in the intestinal
mucosal cells hydrolyzes lactose to its constituent monosaccharides.
It is the least sweet sugar (16% of sucrose).
It is a reducing sugar, it forms osazone crystals and shows mutarotation.