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Biomolecules Part 1

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9 views35 pages

Biomolecules Part 1

Uploaded by

academickeerthan
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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BIOMOLECULES

MONOSACCHARIDES
• Glucose:
- Present in fruits, honey, Ripe grapes etc
Preparation
1. From sucrose (cane sugar):
- Sucrose boiled with dil HCl or H2SO4 in alcoholic solution – glucose
and fructose is formed in equal amounts
- C12H22O11 + H2O  C6H12O6 + C6H12O6
2. From starch:
Commercial method: hydrolysis of starch by boiling with H+ at 393K
(C6H10O5)n + nH2O  nC6H12O6
STRUCTURE OF GLUCOSE

• An aldohexose; also known as dextrose

• The structure of glucose was assigned based on the following


evidence:

1. Molecular formula found to be C6H12O6

2. Prolonged heating with HI forms n-hexane suggesting all 6 C atoms


are linked in straight chain
3. Glucose reacts with hydroxylamine to form oxime; adds molecule of
HCN to form cyanohydrin = confirms presence of carbonyl carbon

4. Treating with a mild oxidising agent (Br2 water) results in formation of


gluconic acid (6 carbon carboxylic acid)
5. Acetylation of glucose gives glucose pentaacetate confirming the presence
of five –OH groups. Since a stable compound, five –OH groups should be
attached

6. Oxidation with HNO3, both glucose and gluconic acid forms a dicarboxylic
acid (saccharic acid) – indicates the presence of primary –OH group
• Exact spatial arrangement given by Fischer

glucose Gluconic Saccharic


acid acid
D(+)-Glucose
D – configuration ; (+) – dextrarotatory nature of molecule
D or L indicates relative configuration of a stereoisomer of a compound with respect to
configuration of another compound (whose configuration is known)
In carbohydrates, configurations are related to a particular isomer of glyceraldehyde
Glyceraldehyde exists in 2 enantiomers:

(+) isomer had D- configuration and (-) isomer has L- configuration


D : H on left, -OH on the right side
All compounds chemically related to D(+) isomers of glyceraldehyde, have D-configuration
Cyclic structure of Glucose
The structure of glucose (Fischer projection) explained most properties of glucose but the
following reactions could not be explained by the structure
1. It didn’t give the Schiff’s test nor the NaHSO3 test despite having an aldehydic group
2. Pentaacetate of glucose does not react with hydroxylamine indicating absence of free –
CHO group
3. Glucose found to exist in 2 different crystalline forms – α and β
α form obtained by crystallization from concentrated solution of glucose at 303K while β
form is obtained by crystallisation from hot and saturated aqeous solution at 371K
- This behaviour cannot be explained by the open structure of glucose
New structure was proposed – one of the –OH group adds to –CHO group and form a cyclic
hemiacetal structure
- Glucose forms six membered ring in which –OH at C-5 is involved in ring formation –
explains the unavailability of –CHO group and existence in 2 forms - anomers
Anomeric Carbon: aldehyde carbon before cyclisation
The cyclic hemiacetals differ only at the anomeric carbons to form two isomers- these isomers
are known as anomers
- Six membered cyclic structure of glucose called pyranose structure (analogous to pyranose)
Fructose
- A ketohexose
- Obtained through hydrolysis of sucrose
- Found in honey, fruits and vegetables
- Used as sweetener in its pure form

Structure of Fructose
- Molecular formula – C6H12O6
- Contains a ketonic group at C-2
- D configuration and laevorotatory in nature = D(-) Fructose
- Exists in two cyclic forms – addition of –OH at C5 to the (C=O) group
- Forms a five membered ring and named as furanose (analogous with compound furan)
DISACCHARIDES
- On hydrolysis with acids yield 2 monosaccharides (both could be same or
different)
- Two monosaccharides are joined together by an oxide linkage

- Glycosidic linkage : linkage between two monosaccharide units


through oxygen atom
- If the reducing groups of the monosaccharides (aldehydic or ketonic group)
are bonded – non reducing sugar
- If even one of the reducing groups of the monosaccharides is free in the
1. Sucrose
- on hydrolysis, gives equimolar mixture of D(+) glucose and D(-) fructose
- Two monosaccharides held together by glycosidic linkage between C1 of α- D- glucose and
C2 of β – D- fructose
- Sucrose is a non reducing sugar since the reducing groups of glucose and fructose are
involved in glycosidic bond linkage
Sucrose is dextrorotatory but after hydrolysis gives
dextrorotatory glucose and laevorotatory fructose
Laevorotation of fructose is greater than dextrarotation
of glucose -the mixture is laevorotatory
Hydrolysis of sugar brings about a change in the sign of
rotation from dextro to laevo and hence the product is
known as invert sugar
2. Maltose:
- Composed of two α- D- glucose units in which C1 of one glucose is linked to C4 of
another glucose unit
- Free aldehyde group can be produced at C1 of the second glucose unit in the solution and
thereby shows reducing property
- Maltose is a reducing sugar
3. Lactose:
Commonly known as milk sugar (found in milk)
Composed of β – D- galactose and C4 of β – D- glucose
C1 of galactose and C4 of glucose
Reducing sugar : free aldehyde group may be produced at C1 of glucose unit
POLYSACCHARIDES
- Contains large number of monosaccharide units joined together by glycosidic linkage
- Most common carbohydrate
- Act as food storage or structural materials
1. Starch
- Main storage polysaccharide in plants
- Found in cereals, roots, tubers, and some vegetables
- polymer of α – glucose and consists of two compoents - Amylose and amylopectin
- Amylose : water soluble component, constitutes 15-20% of starch, unbranched chain of
200-1000 α-D-glucose held together by C1-C4 glycosidic linkage
Amylopectin: insoluble part in water, constitutes 80-85% of starch; a branched chain
polymer of α – glucose units , chain formed by C1-C4 glycosidic linkage and branching
occurs at C1-C6 glycosidic linkage
2. Cellulose:
- Occurs exclusively in plants
- Most abundant organic compound in plant
kingdom
- Predominant constituent in cell wall
- Straight chain polysaccharide composed of
β-D-glucose units joined by glycosidic
linkage between C1 of one glucose unit to
C4 of another glucose unit
Glycogen: carbohydrate stored in animals
• Known as animal starch since its structure is similar to amylopectin (with more
branching)
• Present in liver, muscles and brain

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