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Which one of the following statements regarding the stereoisomers of D-glucose is INCORRECT?
Question

Which one of the following statements regarding the stereoisomers of D-glucose is INCORRECT?

A.

D-mannose is a C-2 epimer of glucose.

B.

D-allose is a C-3 epimer of glucose.

C.

D-galactose is a C-4 epimer of glucose.

D.

D-talose is a C-5 epimer of glucose.

Correct option is D

The term "epimer" refers to a stereoisomer that differs in configuration at only one specific carbon atom. In the context of monosaccharides like D-glucose, epimers are sugars that differ in configuration at a single chiral center other than the anomeric carbon.

Let’s analyze the correct epimeric relationships:

  • D-mannose and D-glucose differ at C-2, so D-mannose is correctly classified as a C-2 epimer of glucose.
  • D-allose and D-glucose differ at C-3, so D-allose is correctly a C-3 epimer of glucose.
  • D-galactose and D-glucose differ at C-4, so D-galactose is a C-4 epimer of glucose.
  • D-talose, however, differs from D-glucose at both C-2 and C-4, not at C-5. Hence, it is not a C-5 epimer. Therefore, statement (d) is incorrect.

Information Booster:

  1. Epimers differ in configuration around only one carbon atom (except the anomeric carbon).
  2. D-mannose and D-glucose differ only at C-2, making D-mannose a C-2 epimer.
  3. D-galactose differs from D-glucose at C-4, classifying it as a C-4 epimer.
  4. D-allose and D-glucose differ at C-3, hence D-allose is a C-3 epimer.
  5. D-talose differs from D-glucose at C-2 and C-4, so it is not a simple epimer at C-5.
  6. The C-5 position in glucose remains the same in all its common aldose epimers, and there is no well-defined C-5 epimer of glucose.
  7. Knowledge of epimers is important in carbohydrate chemistry and stereochemistry, particularly in biochemical transformations and enzymatic reactions.

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