OCCURRENCE, STRUCTURE, BIOLOGICAL IMPORTANCE OF MONOSACCHARIDES

OCCURRENCE AND BIOLOGICAL IMPORTANCE MONOSACCHARIDES

Monosaccharides Occurrence Biochemical importance

Trioses

Glyceraldehyde Found in cells as phosphate Glyceraldehyde 3-phosphate is an

intermediate in glycolysis.

Its 1-phosphate is an intermediate in

Dihydroxyacetone Found in cells as phosphate.
glycolysis.
Tetroses

D-Erythrose It is widespread. Primarily located in Its 4-phosphate is an intermediate in

the cytoplasm of all cells. carbohydrate metabolism.

Pentoses

D-Ribose Widespread as a constituent of It is essential for the structure of

RNA and nucleotides. genetic material RNA, and
nucleotide coenzymes (e.g.,
Riboflavin, Vitamins ATP, NAD+,
NADP+)

D-Deoxyribose As a constituent of DNA It is essential for the structure and

synthesis of DNA

Produced during metabolism It is an important metabolite in

D-Ribulose hexose monophosphate (HMP)
shunt pathway.
As a constituent of glycoproteins and
D-Xylose Involved in the function of
gums
glycoproteins.
It is an intermediate in uronic acid
L-Xylulose It is excreted in urine in essential
pathway.
pentosuria.

Found in heart muscle As a constituent of lyxoflavin of

D-Lyxose
heart muscle
Hexoses
D-Glucose It is a constituent of polysaccharides This is chief source of energy to our
(starch, glycogen, cellulose).and body. The ‘sugar fuel’ of life;
disaccharides (maltose, lactose, excreted in urine of diabetes

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 sucrose). Present in fruits such as patients.
grapes, apple and also present in It is structural unit of cellulose in
honey. plants.

D-Galactose It is a constituent of lactose (a Converted to glucose, failure leads

disaccharide-milk sugar). Present in to galactosemia
milk and dairy products.

D-Mannose Found in plant polysaccharides and Utilized for the structure of

animal glycoproteins.Present in polysaccharides.
D-Fructose Present in fruits, root vegetables (e.g., Its phosphates are intermediates of
sweet potato and onion) honey. glycolysis.s
Present as a constituent of sucrose
and inulin.
Heptoses
D-Sedoheptulose Found in plants Its 7-phosphate is an intermediate in
hexose monophosphate shunt, and
in photosynthesis.

BIOLOGICAL FUNCTIONS OF MONOSACCHARIDES

1. Monosaccharides are an energy source.

2. Glucose is the main fuel for the body cells.
3. About 60-70% of energy for our body is provided by glucose
4. Glucose is a free sugar which circulates in blood and is an important substance for
normal cell functioning.
5. Fructose participates in metabolism.
6. Galactose is found in erythrocytes of individuals with B-type of blood.
7. Ribose is part of deoxyribonucleic acid (DNA) in the chromosomes.
8. Monosaccharides are non essential nutrients.

STRUCTURE OF MONOSACCHARIDES

 Monosaccharides are simple sugars, which possess a free ketone or aldehyde group.
 They cannot be further hydrolyzed. Their chemical formula is CnH2nOn or Cn (H2O) n.
 Monosaccharides are classified two types.
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  Based on functional group it is divided into aldoses (functional group CHO) and
ketoses (Functional group C=O).
 Based on number of carbon atoms it is divided into trioses, tertroses, pentoses,
hexoses and etc.,

Structureof D-Aldoses

Glyceraldehyde (triose) is the simplest monosaccharide with one asymmetric carbon atom.
The configuration of possible D-aldoses starting from D-glyceraldehyde. This is a representation
of Killiani-Fischer synthesis, by increasing the chain length of an aldose, by one carbon at a
time. Thus, starting with an aldotriose (3C), aldotetroses (4C), aldopentoses (5C) and
aldohexoses (6C) are formed. Of the 8 aldohexoses, glucose, mannose and galactose are the most
familiar. Among these, D-glucose is the only aldose monosaccharide that predominantly occurs
in nature.
(Insert Fig 2.2)
Structure of D-Ketoses

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 GLUCOSE

 Glucose is a monosaccharide
 It is a simple sugar
 It is also called as dextrose
 Glucose is a colourless, crystalline solid
 Highly soluble in water and sweet in taste
 It is present in Free State in sweet fruits, honey etc. it is also called as fruit sugar, corn
sugar, grape sugar etc.It is present in sucrose, cellulose, starch and glucogen.
 Glucose is a hexose and contains 6 carbon
 Glucose has a free aldehyde group, hence it is called as an aldohexoses
 The molecular formula is C6H12O6
 the structure of glucose can be represented as straight chain structure as well as ring or
cyclic structure.
 There are 3 types of structures, namely, straight chain, Fischer, projections and Haworth
structure.

 Glucose contains 4 assymmetric carbon atoms (2,3,4 and 5) and 16 isomers.

 It is optically active and dextrorotatory
 It shows mutarotation

Functions of Glucose
 Glucose is the chief source of energy
 It is the fuel for cellular respiration
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  It is the precursor for the synthesis of sucrose, starch, cellulose and glycogen
 Glucose is the raw material for glycolysis, kerbs cycle and electron transport chain.
 It is used for ATP synthesis
 It binds with proteins and lipids and forms glycoproteins and glycolipids.
 It is the precursor for the synthesis of vitamin C and etc
 5% solution is used for intravenous therapy for rehydration and energy.

GENERAL PROPERTIES OF MONOSACCHARIDES (GLUCOSE)

1. It can be solid or liquid, sweet in taste.

2. It has no odor soluble in water and acetic acid.
3. Its molecular formula C6H12O6
4. Glucose can be called as aldohexose as well as dextrose.
5. The oxime is formed when glucose or fructose reacts with hydroxylamine. This reaction
can confirm the presence of the aldehyde or carbonyl group.
6. On the reaction of glucose with a mild oxidizing agent like bromine water, the glucose
gets oxidized to a carboxylic acid that contains six carbon atoms, this indicates that the
carbonyl group is present as an aldehyde group.
7. The presence of OH group is confirmed after the acetylation of glucose with acetic acid
which gives glucose penta acetate.
8. Glucose as well as gluconic acid both yields dicarboxylic acid and saccharic acid on
oxidation with nitric acid. The presence of primary alcohol is indicated by this.
9. Glucose reacts with phenylhydrazine and forms glucose crystals.

Haworth projection or Ring structure of Fructose

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STEREO ISOMERISM AND OPTICAL ISOMERISM OF SUGARS

Isomers are compounds having same molecular formula but different molecular
structures. Monosaccharides show isomerism, it has same number of atoms and the same type of
groups in their structures. But they are entirely different substances. For example C 6H1206 is the
molecular formula for hexoses. There are 16 different hexoses possessing similar structure as
that of glucose like,

CHO-CHOH-CHOH-CHOH-CHOH-CH2OH

The spatial arrangement of certain constituent groups like hydrogen and hydroxyl in each
of these varies. This phenomenon is called stereoisomerism or space isomerism and the sugars
are called stereoisomers.

Examples of stereoisomers having the same molecular formula but different space
formula are,

ASYMMETRY OF CARBON ATOM AND OPTICAL ACTIVITY

Carbohydrates exhibit an important property called optical activity. It is closely related to

the asymmetry of carbon atom (a carbon atom to which four different groups or atoms are
attached).

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 In glyceraldehydes the second carbon atom is asymmetric. In D-
glyceraldehydes the OH-group is to the right side and H-group is to the left. In L-
glyceraldehydes the OH-group is to the left of the asymmetric carbon atom and H-group to the
right. But there are sugars with two or more asymmetric carbon atoms.

These two isomers are not superimposable images as they are mirror images of each
other. All such isomers are said to exhibit optical isomerism, which involves optical rotation.
Monosaccharides containing asymmetric carbon atoms are glucose, fructose, mannose, galactose
and glyceraldehydes.

OPTICAL ISOMERISM
Optical isomerism specifies the peculiar effect undergone by solutions of isomers by
plane polarized light.

Optical Isomer
When a beam of polarized light is passed through a solution exhibiting optical activity, it
will be rotated to the right or to the left in accordance with the type of compound, i.e. the optical
isomer, which is present. A compounds which causes rotation of polarized light to the right is
said to be dextrorotatory and a plus (+) sign is used to designate the fact. Rotation of the beam to
the left (levorotatory action) is designated by a minus (-) sign.

When equal amounts of dextrorotatory and levorotatory isomers are present, the resulting
mixture has no optical activity since the activities of each isomer cancel the other. Such a
mixture is said to be racemic or a DL mixture.

Figure of Plane polarized light and optical rotation.

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 (a. Plane polarized light rotated in to anticlockwise direction – L form, b. plane polarized
light in to clockwise direction – D form, c. racemate – no overall effect – DL form)

ANOMERIC FORM OF SUGARS:

The cyclic forms of carbohydrates can exist in two forms, α- and β- based on the position
of the substituent at the anomericcarbon atom.The α- and β form of the sugars are called
anomers. Example: α- and β form of D-Glucose

 In the α- form, the exocyclic O group at the anomeric center is on the

opposite face to the -CH2OH group, and

 In the β- form, the exocyclic O group at the anomeric center is on the

same face as the -CH2OH group.
 In ‘D’ series the hydroxyl group of C-5 is on the right, whereas the
hydroxyl group of C-5 in the ‘L’-series is on the left.

MUTAROTATION

Mutarotation means, changing of optical rotation. Tanret explained that when a solution
of freshly prepared crystalline glucose of α-D form is observed in a polariscope, its initial
specific rotation which is + 112° gradually decreases and finally becomes steady at +52.5°.

 When the solution of pure crystals of β-D glucose is observed in a

polariscope, the initial specific rotation of +19° gradually increases and

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 finally becomes steady at +52.5°. The change in rotation is illustrates as
+112° +52.5° + +19°

(α-D-glucose) (β-D-
glucose)

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