Lec 9 BioC

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Derived monosaccharides:

 Several compounds that are derived from monosaccharides are of importance in plant metabolism.
 They are also referred to as modified monosaccharides.
 The important functional groups present in monosaccharides are hydroxyl and carbonyl groups.
 The hydroxyl group forms esters, usually with phosphoric acid or is replaced by a hydrogen or amino group.
1. Sugar esters:
 As carbohydrates have hydroxyl groups, they are able to participate in reactions with carboxylic
acids and carboxylic acid derivatives to form esters. (O-acyl derivatives)
 An important type of carbohydrate ester in plant metabolism is the phosphate ester that are
formed with biological phosphorylating agents such as ATP catalyzed by appropriate enzymes.
 Glucose -6-phosphate
 α -D-Fructose-1,6-bisphosphoric acid
 Draw the structure of α -D-Fructose-1,6-bisphosphoric acid.
 How are such phosphate esters formed in plants? Give one example along with the specific
enzyme that catalyses this reaction.

2. Deoxysugars:
In sugars, the hydroxyl group is replaced by hydrogen to produce deoxy sugars (devoid of oxygen).
 β –D-2-Deoxyribofuranose
 L-fucose
 L- rhamnose.
o Draw the ring structures of β –D-ribofuranose and β –D-2-Deoxyribofuranose.
o L-fucose and L-rhamnose are deoxy sugars of ________ and___________ respectively derived
due to replacement of OH at __________ carbon.
o Where are the above three deoxysugars present in plants?

3. Amino sugars:
 The hydroxyl group, usually at C-2, is replaced by an amino group to produce aminosugars such as
glucosamine, galactosamine and mannosamine.
 The amino group may be condensed with acetic acid to produce N-acetyl aminosugars, for example, N-
acetyl glucosamine.
o Give two examples where N-acetyl glucosamine in present in plant cells.

 The carbonyl group undergoes reduction or oxidation to produce number of derived monosaccharides.
4. Reduction Products:
 Polyols (alditols) :Sugar alcohols
 Both aldoses and ketoses are reduced to polyhydric alcohols (polyols) when treated with enzymes, sodium
amalgam, and hydrogen under high pressure with catalyst or sodium borohydride (NaBH).
 Write the respective alcohols for the following sugars:
o Glucose ____________
o Fructose ____________
o Mannose ____________
o Glyceraldehyde ____________
o Erythrose ____________

 What any two functions of polyols in plants and two uses in food industry ?
 Find out what is inositol and its phosphorylated form and its role in plants (any one role)?

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