Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 35MP
Interpretation Introduction

Interpretation:

Suitable mechanisms for the three steps involved in the biosynthesis of L-fucose from GDP-D-mannose shown are to be proposed.

Concept introduction:

Step 1 involves three reactions: i) Oxidation of a secondary alcohol to a ketone by NAD+. ii) Dehydration to an enone iii) 1,4-Addition of NaDH to the enone iv) Protonation and loss of NAD+.

Step 2 involves two epimerization reactions, one involves the acidic site of the enzyme and other involves the basic site of the enzyme.

Step 3 involves attack of NADH on the carbonyl group and protonation.

To propose:

Suitable mechanism for the three steps involved in the biosynthesis of L-fucose from GDP-D-mannose shown.

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