The amine 1 is an anti-cancer drug that is made using the following reaction, which is catalysed by an imine reductase: OHC. .CO2R .CO2R NADPH NH2 imine reductase (racemic) 1 (99.7% e.e) a) Write a curly-arrow mechanism for this reaction that clearly shows the involvement of NADPH.

Biochemistry
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Chapter1: Biochemistry: An Evolving Science
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Answer a to d for amine reaction

Answer ALL parts a) – d).
The amine 1 is an anti-cancer drug that is made using the following reaction, which
is catalysed by an imine reductase:
ОНС
CO2R
NADPH
.CO2R
NH2
imine
reductase
(racemic)
1 (99.7% e.e)
a) Write a curly-arrow mechanism for this reaction that clearly shows the involvement
of NADPH.
b) State the maximum yield of this reaction and briefly justify your answer.
c) State two problems with using this reaction to obtain amine 1 in multi-gram
amounts.
d) An engineered ketoreductase can be used to catalyse the following reaction:
.CO2R
OHC.
.CO2R
Но
+ NADP+
+ NADPH + H+
ketoreductase
2
Propose three advantages of using the ketoreductase and the imine reductase in
an enzyme cascade to convert the alcohol 2 into the amine 1.
Transcribed Image Text:Answer ALL parts a) – d). The amine 1 is an anti-cancer drug that is made using the following reaction, which is catalysed by an imine reductase: ОНС CO2R NADPH .CO2R NH2 imine reductase (racemic) 1 (99.7% e.e) a) Write a curly-arrow mechanism for this reaction that clearly shows the involvement of NADPH. b) State the maximum yield of this reaction and briefly justify your answer. c) State two problems with using this reaction to obtain amine 1 in multi-gram amounts. d) An engineered ketoreductase can be used to catalyse the following reaction: .CO2R OHC. .CO2R Но + NADP+ + NADPH + H+ ketoreductase 2 Propose three advantages of using the ketoreductase and the imine reductase in an enzyme cascade to convert the alcohol 2 into the amine 1.
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