Multiple Choice
Which of the following sugars undergoes mutarotation in neutral aqueous solution?
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9. Carbohydrates
Mutarotation
Multiple Choice
Which of the following forms of glucose or its derivatives is capable of undergoing mutarotation?
A
D-glucose (in aqueous solution)
B
D-glucose-6-phosphate
C
Methyl-b-D-glucopyranoside
D
D-gluconic acid
Verified step by step guidance1
Understand the concept of mutarotation: Mutarotation is the process by which the alpha and beta anomers of a cyclic sugar interconvert in aqueous solution. This requires the sugar to have a free hydroxyl group on the anomeric carbon, allowing the ring to open and close.
Analyze D-glucose (in aqueous solution): D-glucose has a free hydroxyl group on its anomeric carbon, enabling the ring to open and close, thus allowing mutarotation.
Examine D-glucose-6-phosphate: The phosphate group is attached to the sixth carbon, not the anomeric carbon. The anomeric carbon still has a free hydroxyl group, so mutarotation can occur.
Evaluate Methyl-β-D-glucopyranoside: In this derivative, the anomeric hydroxyl group is replaced by a methyl group, preventing the ring from opening. Therefore, mutarotation cannot occur.
Consider D-gluconic acid: D-gluconic acid is an oxidized form of glucose where the aldehyde group at the anomeric carbon is converted to a carboxylic acid. This modification prevents the ring from opening, so mutarotation cannot occur.
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