5.1.2.2: mandelate racemase
This is an abbreviated version!
For detailed information about mandelate racemase, go to the full flat file.
Word Map on EC 5.1.2.2
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5.1.2.2
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s-mandelate
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kenyon
-
alpha-proton
-
muconate
-
gerlt
-
1,1-proton
-
benzohydroxamate
-
petsko
-
kozarich
-
mitra
-
galactarate
-
benzoylformate
-
d-glucarate
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ransom
-
synthesis
-
analysis
-
biotechnology
- 5.1.2.2
- s-mandelate
-
kenyon
-
alpha-proton
- muconate
-
gerlt
-
1,1-proton
- benzohydroxamate
-
petsko
-
kozarich
- mitra
- galactarate
- benzoylformate
- d-glucarate
-
ransom
- synthesis
- analysis
- biotechnology
Reaction
Synonyms
mandelate racemase, mandelic acid racemase, mdlA, MR, racemase, mandelate
ECTree
5.1.2.2 mandelate racemaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 5.1.2.2 - mandelate racemase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2R)-2-(4-bromophenyl)-2-hydroxyacetamide
?
-
22% of the activity with (R)-mandelate
-
-
?
(2R)-2-furyl(hydroxy)acetic acid
?
-
24% of the activity with (R)-mandelate
-
-
?
(2R)-2-hydroxy-2-phenylacetamide
?
-
15% of the activity with (R)-mandelate
-
-
?
(2R)-2-hydroxy-3-(1-H-imidazol-1-yl)propanoic acid
?
-
5.4% of the activity with (R)-mandelate
-
-
?
(2R)-2-hydroxypentanoic acid
?
-
1% of the activity with (R)-mandelate
-
-
?
(2R)-2-naphthylglycolate
(2S)-2-naphthylglycolate
a non-natural substrate
-
-
?
(2R)-3-furyl(hydroxy)acetic acid
?
-
38% of the activity with (R)-mandelate
-
-
?
(2R)-cyclohex-1-en-1-yl(hydroxy)acetic acid
?
-
50% of the activity with (R)-mandelate
-
-
?
(2R)-hydroxy(2-naphthyl)acetic acid
?
-
26% of the activity with (R)-mandelate
-
-
?
(2S)-hydroxy(2-thienyl)acetic acid
?
-
59% of the activity with (R)-mandelate
-
-
?
(R)-(E)-2-hydroxy-3-pentenoic acid
?
-
36% of the activity with (R)-mandelate
-
-
?
(R)-(E)-2-hydroxy-4-phenyl-3-butenoic acid
?
-
53% of the activity with (R)-mandelate
-
-
?
(R)-3-chloromandelate
(S)-3-chloromandelate
a non-natural substrate
-
-
?
(S)-mandelic acid amide
(R)-mandelic acid amide
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activity is enhanced by an electron-withdrawing substituent in the phenyl moiety
-
?
(S)-vinylglycolate
(R)-vinylglycolate
two-step quite symmetric process through a dianionic enolic intermediate that is formed after the abstraction of the alpha-protein of vinylglycolate by a basic enzymatic residue and is then reprotonated by another residue
-
?
2-hydroxybut-3-enoic acid
?
-
35% of the activity with (R)-mandelate
-
-
?
4-bromo-(R)-mandelate
4-bromo-(S)-mandelate
-
376% of the activity with (R)-mandelate
-
-
r
4-chloro-(R)-mandelate
4-chloro-(S)-mandelate
-
326% of the activity with (R)-mandelate
-
-
r
4-fluoro-(R)-mandelate
4-fluoro-(S)-mandelate
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96% of the activity with (R)-mandelate
-
-
r
4-hydroxy-(R)-mandelate
4-hydroxy-(S)-mandelate
-
45% of the activity with (R)-mandelate
-
-
r
4-methoxy-(R)-mandelate
4-methoxy-(S)-mandelate
-
17% of the activity with (R)-mandelate
-
-
r
5-chloro-(R)-mandelate
5-chloro-(S)-mandelate
-
61% of the activity with (R)-mandelate
-
-
r
(R)-mandelate
(S)-mandelate
wild-type enzyme shows slightly higher affinity for (S)-mandelate than for (R)-mandelate, but catalyzes the turnover of (R)-mandelate slightly more rapidly
-
-
r
(S)-2-chloromandelate
(R)-2-chloromandelate
binding structure
-
-
r
(S)-2-chloromandelate
(R)-2-chloromandelate
binding structure
-
-
r
(S)-2-hydroxy-3-butenoic acid
(R)-2-hydroxy-3-butenoic acid
-
maximal racemization rate is 35% relative to mandelate
-
?
(S)-mandelate
(R)-mandelate
catalyzes the Mg2+-dependent 1,1-proton transfer that interconverts the enantiomers, catalysis is done via a two-base mechanism
-
-
r
D-mandelate
L-mandelate
-
strictly inducible enzyme. Inducers: D-mandelate, L-mandelate, benzoylformate
-
-
?
D-mandelate
L-mandelate
-
first enzyme in the bacterial pathway that converts mandelic acid to benzoic acid
-
-
?
D-mandelate
L-mandelate
-
first enzyme of pathway of oxidation of D,L-mandelate that permits certain strains of Pseudomonas putida to use mandelate as a sole source of carbon and energy
-
-
?
p-(bromomethyl)mandelate
p-(methyl)benzoylformate + Br-
-
-
i.e. alpha-carboxy-alpha-hydroxy-p-xylylene
?
additional information
?
-
-
not racemized: 4-hydroxy-3-methoxymandelate, 3,4-dihydroxymandelate
-
-
?
additional information
?
-
-
efficient racemization of 2-hydroxy-2-heteroaryl-acetic acid derivatives. Steric limitations for aryl-substituted mandelate derivatives are elucidated to be particularly striking for o-substituents, whereas m- and p-analogues are freely accepted as well as heteroaryl and naphthyl analogs. The electronic character of substituents is found to play an important role: whereas electron-withdrawing substituents dramatically enhance the racemization rates, electron-donating analogs cause a depletion
-
?
additional information
?
-
-
no activity with phenyl glycine and mandelic acid hydrazide
-
?
additional information
?
-
mandelate racemase catalyzes the Mg2+-dependent 1,1-proton transfer that interconverts the enantiomers of mandelate
-
-
?
additional information
?
-
-
mandelate racemase catalyzes the Mg2+-dependent 1,1-proton transfer that interconverts the enantiomers of mandelate
-
-
?
additional information
?
-
substrate recognition and binding method, overview. Mandelate racemase from Pseudomonas putida catalyzes the interconversion of the enantiomers of mandelic acid and a variety of aryl- and heteroaryl-substituted mandelate derivatives. beta,gamma-Unsaturation is not an absolute requirement for catalysis and that mandelate racemase can bind and catalyze the racemization of (S)- and (R)-trifluorolactate. The enzyme catalyzes hydrogen-deuterium exchange at the alpha-postion of trifluorolactate
-
-
?
additional information
?
-
-
substrate recognition and binding method, overview. Mandelate racemase from Pseudomonas putida catalyzes the interconversion of the enantiomers of mandelic acid and a variety of aryl- and heteroaryl-substituted mandelate derivatives. beta,gamma-Unsaturation is not an absolute requirement for catalysis and that mandelate racemase can bind and catalyze the racemization of (S)- and (R)-trifluorolactate. The enzyme catalyzes hydrogen-deuterium exchange at the alpha-postion of trifluorolactate
-
-
?
additional information
?
-
enzyme activity detection in the high-throughput screening method of enzymes involving the racemization of (S)-2-chloromandelate, method evaluation, overview
-
-
?
additional information
?
-
enzyme activity detection in the high-throughput screening method of enzymes involving the racemization of (S)-2-chloromandelate, method evaluation, overview
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-
?
