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The enantiomer of α−D−(+) -glucose isβ−D−(+) -glucoseα -D- (−) -glucoseα -L- (−) -glucoseβ−L−(−) -glucose

Question

The enantiomer of α−D−(+) -glucose is

  • β−D−(+) -glucose
  • α -D- (−) -glucose
  • α -L- (−) -glucose
  • β−L−(−) -glucose
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Solution

The enantiomer of α−D−(+) -glucose is α -L- (−) -glucose.

Enantiomers are stereoisomers that are mirror images of each other. In the case of glucose, the D and L notations refer to the configuration of the highest numbered chiral carbon (carbon with four different groups attached), which is the carbon farthest from the aldehyde or ketone group.

In D-glucose, this carbon has the same configuration as in D-glyceraldehyde (hydroxyl group on the right in a Fischer projection), while in L-glucose, it has the same configuration as in L-glyceraldehyde (hydroxyl group on the left).

The α and β notations refer to the configuration of the anomeric carbon (carbon of the aldehyde or ketone group). In α-glucose, the hydroxyl group on the anomeric carbon is on the opposite side (trans) of the ring from the CH2OH group on the highest numbered chiral carbon, while in β-glucose, it is on the same side (cis).

Therefore, the enantiomer of α−D−(+) -glucose, which has the hydroxyl group on the right at the highest numbered chiral carbon and on the opposite side of the ring at the anomeric carbon, is α -L- (−) -glucose, which has the hydroxyl group on the left at the highest numbered chiral carbon and on the opposite side of the ring at the anomeric carbon.

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