Biomolecules

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BIOMOLECULES

I. CARBOHYDRATES
• Optically active polyhydroxy aldehydes or ketones or the compounds that produce such units
on hydrolysis.
• Since some carbohydrates are sweet, they are also called sugars or saccharides.

Types of Carbohydrates:
1) Monosaccharides: A carbohydrate that cannot be hydrolyzed further to give simpler unit.
Examples: glucose, fructose, etc.
• About 20 natural monosaccharides are known.
• Monosaccharides can be further divided as:

No. of C Atoms General Term If Aldehyde If Ketone


3 Triose Aldotriose Ketotriose
4 Tetrose Aldotetrose Ketotetrose
5 Pentose Aldopentose Ketopentose
6 Hexose Aldohexose Ketohexose
7 Heptose Aldoheptose Ketoheptose

2) Oligosaccharides: Carbohydrates that give 2–10 monosaccharides on hydrolysis.


• They can be disaccharides, tri-saccharides, etc.

3) Polysaccharides: Carbohydrates that give many monosaccharide units on hydrolysis. Examples:


starch, cellulose, glycogen, gums, etc.
• Not sweet ⇒ also called non-sugars.

4) Reducing or non-reducing sugars: Carbohydrates that reduce Fehling’s solution and Tollens’
reagent are called reducing sugars.
• All monosaccharides (both aldoses and ketoses) are reducing in nature.
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GLUCOSE:
• Also called dextrose.

Methods of Preparation:
(1) By hydrolysis of sucrose in boiling HCl or H2SO4 solution:
H+
C12H22O11 + H2O → C6H12O6 (glucose) + C6H12O6 (fructose)

(2) By hydrolysis of starch in boiling H2SO4:


H+
(C6H10O5)n + n H2O → n C6H12O6 (glucose)

Structure Determination of Glucose:

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The D and L Notation:


• In the Fischer projection of a carbohydrate, if the –OH group joined to the lowermost chiral
carbon is on the right, then the compound is a D-sugar.
• If the –OH group is on the left, then the carbohydrate is an L-sugar.
• D and L are not related to the optical activity of the compound.
• D and L configurations indicate the relation of a stereoisomer with glyceraldehyde.
• Generally, natural sugars are D-sugars.
• The D- and L- forms of a carbohydrate are related as mirror images.
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Cyclic Structure of Glucose:


Limitations of open-chain structure:
• Glucose does not react with Schiff’s reagent and NaHSO3.
• The pentaacetate of glucose does not react with NH2OH, indicating the absence of free –CHO
group.
• Glucose exists in two different crystalline forms — α and β. The crystallization from conc.
glucose solution at 303 K gives α- glucose (m.p. 419 K), whereas crystallization from hot and
saturated aqueous glucose at 371 K gives β-glucose (m.p. 423 K).

Mutarotation:
• Slow change in the optical rotation of a compound to an equilibrium value.
• Non-reducing sugars do not show mutarotation.
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FRUCTOSE:
• Found in fruits, honey and vegetables; sweetest natural sugar.

Structure of Fructose: (Leave 1 page – one side.)

DISACCHARIDES:
• Two monosaccharide units joined together by glycosidic linkage.
• Glycosidic linkage: An oxide linkage between two monosaccharide units formed by the loss
of a water molecule.

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