Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 25, Problem 25.16P
Interpretation Introduction

(a)

Interpretation:

The structure of UDP-glucose is to be determined.

Concept introduction:

The structure of UDP-glucose is similar to UDP-galactose only the galactose ring is replaced with glucose.

Interpretation Introduction

(b)

Interpretation:

The reaction for the sucrose biosynthesis is to be drawn and reaction occurs with inversion or retention of stereochemistry at anomeric carbon of UDP-glucose is to be determined.

Concept introduction:

The sucrose biosynthesis is occurred by nucleophilic attack of fructose to anomeric carbon of UDP-glucose and the reaction proceeds through SN1 reaction by formation of oxygen stabilized carbocation. The stereochemistry of at anomreic carbon can be determined by the approach of attacking fructose on anomeric carbon.

Interpretation Introduction

(c)

Interpretation:

The role of an arginine (Arg) residue and lysine (Lys) residue in the synthase mechanism is to be explained.

Concept introduction:

The negative charge on phosphate esters can be stabilized by metal ion or the positively charged groups on the active-site amino acids.

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