Q. 13.27 - An Introduction to General, Organic, and Biological Chemistry

Question

An infant with galactosemia can utilize$D-$glucose in milk but not $D-$galactose. How does the Fischer projection of$D-$galactose differ from that of $D-$glucose?

Step-by-Step Solution

Answer

Epimers are diastereoisomers with several stereogenic centres but only one stereogenic centre.

Step 1 : Introduction

•  The Fischer projection, a way of visualising three-dimensional structures of molecules on a page.
• Horizontal lines represent bonds that are projecting toward the viewer from the plane of the paper, while vertical lines represent bonds that are projecting away from the spectator.
• In this problem, we have to explain the structural difference (in Fischer projections) of $D-$galactose from $D-$glucose.

Step 2 : Explanation of   D -galactose from   D - glucose.

• $D-$galactose and $D-$glucose are both aldohexoses (six carbons and an aldehyde group) with a right-hand penultimate hydroxy group.
• We can observe that the sole change in the structure of both sugars is on carbon number four. The stereogenic centre on $D-$carbon galactose's number four differs from that of $D-$gluocse.
• $D-$glucose and $D-$galactose are hence $C_4$ epimers.

Step 3 : Draw the structure of D - glucose and D - galactose

Epimers are diastereoisomers with several stereogenic centres but only one stereogenic centre.