Module 9: Enzymes in Functional
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Lecture15: Enzymes in Functional
Group Transformation
(Topic Contd. Lecture No.15
-
30)
(Topic Contd. Lecture No.15
30)
1
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Enzyme Functional Group - Biochemistry - Lecture Slides, Slides of Biochemistry
This lecture is part of lecture series on Enzymes in Functional Group Transformation course. This lecture was delivered in Biochemistry class at Deenbandhu Chhotu Ram University of Science and Technology. This lecture main points are: Enzymes, Transformation, Oxidoreductases, Transferases, Lyases, Isomerases, Ligases, Alcohols
Typology: Slides
2011/2012
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Module 9: Enzymes in Functional
G
T
f
ti
Group Transformation
Lecture15: Enzymes in Functional
Group Transformation
(Topic Contd. Lecture No.15 -30)(Topic Contd. Lecture No.
1 Docsity.com
The Main Enzyme classes
1. Oxidoreductases
Oxidation-reduction reactions
2. Transferases
Transfer of functional groups
3. Hydrolases
Hydrolysis reactions
3.
yd o ases
yd o ys s
eact o s
4. Lyases
Group elimination (forming new bonds)
5 Isomerases
Isomerization reactions
5. Isomerases
Isomerization reactions
6. Ligases
Bond formation coupled withatriphosphate cleavage
In
the
subsequent
section
we
will
discuss
the
synthetic
potentials
of
oxidoreductases, hydrolases, lyases and isomerases due to their wide applicabilityin organic synthesis.
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Dehydrogenase mechanismDehydrogenase
mechanism
• A holoenzyme (an enzyme with its
A holoenzyme (an enzyme with itscoenzyme) binds a carbonyl compound
• A hydride on the coenzyme is transferred• A hydride on the coenzyme is transferred
to the carbonylTh
l^
th
d
t
• The enzyme releases the product• The oxidized coenzyme is transferred
back into the reduced form
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O
P
P
CONH HR
Hs
CONH Hs
HR
L
S
P
P
N
CONH
2
N ADPR
CONH
2
ADPR
ADPR
L
S
OH
L
S
P1: Pro-
S , si face from
M. javanicus
P2: Pro-
R
si face from
Pseudomonas
sp. or
Lactobacillus keifir
P3: Pro-
R
re face, from yeast, horse liver
P4: Pro
S
re face unknown
P4: Pro-
S^
re face, unknown.
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Coenzyme regenerationCoenzyme
regeneration
O
a^
b
R
R'
O
R
R'
OH
R^
R'
O
R
R'
OH
Enzyme 1
Enzyme 1
a.^
b.
NADH
NAD
+^
NADH
NAD
O
OH
CO
HCO H
CO
2
HCO
H 2
Enzyme 2
Auxiliary substrate
Enzyme 2
Auxiliary substrate
Auxiliary substrate
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Example of reduction using the formate/formateExample
of reduction using the formate/formate
dehydrogenase NADH-recycling system
Cl
O
CO
Et 2
Cl
OH
CO
Et^2
carbonyl reductase from Rhodococcus erythropolis^ NAD
+^
HCO
H
NAD
+, HCO
H 2
formate dehydrogenas
Yield = 100%; ee = 99%
O
CO
Et 2
OH
CO
Et 2
carbonyl reductase from Rhodococcus erythropolis^ NAD
+^
HCO
H
NAD
+, HCO
H 2
formate dehydrogenas
Yield = 49%; de = 95%; ee = 99%
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OH
OH
OH
R -ketoreductase
O
R
R'
R
R'
R
R'
R -ketoreductase
R
R'
O
Isolated enzyme
Whole cell(mixture of R/S ketoreductases)
OH
OH
OH
Unnatural substrate
R
R'
R
R'
R
R'
S -ketoreductase
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Synthesis of both enantiomers using one microorganism by choosing appropriate conditions
R^
R' O
R^
R' OH
R^
R' OH
inhibitor of R-enzymeor activator of S-enzyme
inhibitor of S-enzymeor activator of R-enzyme
R^
R
Unnatural substrate
(S)
(R) Docsity.com