A Hy N-CHL=° %3D CH CH2 E C H O H3C-" %3D +N-フ CH3 こ-0-C内 CH2 E CHA E E-Ch マェ *ナ ミェ Chymotrypsin can catalyze the following reaction, with a simple substrate that mimics its natural substrate: H,0 HO H3 C- - 0 - CH3 CHy coo + HzN ti-ocHs CH3 N-Ac-Phe Ala-O-Me + O°H + This reaction catalyzed by chymotrypsin is essentially irreversible. Thus if chymotrypsin is mixed with the products of its reaction, there is virtually no reaction in the reverse direction. + N-acetyl-Phe-Ala-O-methyl ester However, the individual steps of the chymotrypsin-catalyzed reaction are all reversible, in the active site of the enzyme, and chymotrypsin will catalyze the following "exchange" reaction: N-Ac-Phe-Ala-O-Me + Gly → N-Ac-Phe-Gly + Ala-O-Me Which one of the structures given below is a reaction intermediate that would be involved in this exchange reaction? Explain briefly how the intermediate that you chose would enable the exchange reaction to occur.

Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
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A
Hy N-CHL=°
%3D
CH
CH2
E
C
H O
H3C-"
%3D
+N-フ
CH3
こ-0-C内
CH2
E
CHA
E
E-Ch
マェ
*ナ
ミェ
Transcribed Image Text:A Hy N-CHL=° %3D CH CH2 E C H O H3C-" %3D +N-フ CH3 こ-0-C内 CH2 E CHA E E-Ch マェ *ナ ミェ
Chymotrypsin can catalyze the following reaction, with a simple substrate that mimics its natural
substrate:
H,0
HO
H3 C-
- 0 - CH3
CHy
coo + HzN ti-ocHs
CH3
N-Ac-Phe
Ala-O-Me
+ O°H +
This reaction catalyzed by chymotrypsin is essentially irreversible. Thus if chymotrypsin is mixed
with the products of its reaction, there is virtually no reaction in the reverse direction.
+
N-acetyl-Phe-Ala-O-methyl ester
However, the individual steps of the chymotrypsin-catalyzed reaction are all reversible, in the
active site of the enzyme, and chymotrypsin will catalyze the following "exchange" reaction:
N-Ac-Phe-Ala-O-Me + Gly → N-Ac-Phe-Gly + Ala-O-Me
Which one of the structures given below is a reaction intermediate that would be involved in this
exchange reaction? Explain briefly how the intermediate that you chose would enable the
exchange reaction to occur.
Transcribed Image Text:Chymotrypsin can catalyze the following reaction, with a simple substrate that mimics its natural substrate: H,0 HO H3 C- - 0 - CH3 CHy coo + HzN ti-ocHs CH3 N-Ac-Phe Ala-O-Me + O°H + This reaction catalyzed by chymotrypsin is essentially irreversible. Thus if chymotrypsin is mixed with the products of its reaction, there is virtually no reaction in the reverse direction. + N-acetyl-Phe-Ala-O-methyl ester However, the individual steps of the chymotrypsin-catalyzed reaction are all reversible, in the active site of the enzyme, and chymotrypsin will catalyze the following "exchange" reaction: N-Ac-Phe-Ala-O-Me + Gly → N-Ac-Phe-Gly + Ala-O-Me Which one of the structures given below is a reaction intermediate that would be involved in this exchange reaction? Explain briefly how the intermediate that you chose would enable the exchange reaction to occur.
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