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Chapter 11: Q 11-11-33 E (page 350)

Metabolism of S-adenosylhomocysteine (Section 11-6) involves the following sequence. Propose a mechanism for the second step.

Short Answer

Expert verified

The mechanism for the metabolism of S-adenosylhomocysteine is,

Step by step solution

01

Metabolism of S-adenosylhomocysteine

The metabolism of S-adenosylhomocysteine is done by treating it with a NAD+base, and the leaving group is homocysteine. This process takes place in two steps, first is oxidizing alcohol to the ketone of S-adenosylhomocysteine, and in the second step, homocysteine leaves the compound.

02

The mechanism for the metabolism of S-adenosylhomocysteine

In the first step, oxidizes alcohol of S-adenosylhomocysteine to a ketone group and is shown below as,

The mechanism for the metabolism of S-adenosylhomocysteine

03

The mechanism for the second step of metabolism of S-adenosylhomocysteine

In the second step, the product formed in the first step is reacted with a base that brings about an E1cB elimination reaction. The leaving group in this is homocysteine.

The mechanism for the second step

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Most popular questions from this chapter

Question: There are eight diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stable chair conformation. One isomer loses HCl in an E2 reaction nearly 1000 times more slowly than the others. Which isomer reacts so slowly, and why?

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