
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question

Transcribed Image Text:Creatine is a naturally occurring compound that helps
provide energy to cells in the body, especially muscle
cells. Draw an S2 mechanism that shows how creatine
is produced from guanidoacetate and SAM (see
Problem 8.66).
H2N-
H2N
NH2
NH2
Guanidoacetate
Creatine

Transcribed Image Text:(S)-Adenosylmethionine (SAM) is a cosubstrate that is involved in biological methyl group transfers. SAM is believed to be
produced by an Sy2 type of reaction between methionine and ATP, as shown below.
H,N
H,N
N:
N
N
H3N.
H3N
CO2
ОН ОН
ОН ОН
Methionine
ATP
SAM
(a) Draw the appropriate curved arrows for this reaction.
(b) Suggest why the reaction takes place with S as the nucleophilic atom instead of one of the negatively charged O
atoms on methionine.
0=P-
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