Chapter 19.SE, Problem 50MP

Interpretation Introduction

Interpretation:

Glutamate is converted into α- ketoglutarate by the reaction sequence shown below.

The structure of the imine intermediate is to be shown and mechanisms for both steps are to be proposed.

Concept introduction:

Transfer of a hydride ion from the glutamate to NAD+ followed by the deprotonation of the intermediate formed will yield the imine.

The attack of water on the protonated imine and subsequent deprotonation yield a carbinolamine intermediate. The intermediate on further reaction breaks to yield a ketone and amine/ammonia as products.

To show:

The structure of the imine intermediate formed when glutamate is converted into α- ketoglutarate by the reaction sequence shown below and to propose mechanisms for both steps.