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IUBMB CommentsThis enzyme, along with N-carbamoylase (EC 3.5.1.77 and EC 3.5.1.87) and hydantoinase, forms part of the reaction cascade known as the "hydantoinase process", which allows the total conversion of D,L-5-monosubstituted hydantoins into optically pure D- or L-amino acids . The enzyme from Pseudomonas sp. (HyuE) has a preference for hydantoins with aliphatic substituents, e.g. D- and L-5-[2-(methylsulfanyl)ethyl]hydantoin, whereas that from Arthrobacter aurescens shows highest activity with arylalkyl substituents, especially 5-benzylhydantoin, at the 5-position . In the enzyme from Sinorhizobium meliloti, Cys76 is responsible for recognition and proton retrieval of D-isomers, while Cys181 is responsible for L-isomer recognition and racemization .
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(5S)-5-(1H-indol-2-ylmethyl)-3-methylimidazolidine-2,4-dione
(5R)-5-(1H-indol-2-ylmethyl)-3-methylimidazolidine-2,4-dione
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20.2% of the activity with (5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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(5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
(5R)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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-
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r
(5S)-5-(2-methylpropyl)imidazolidine-2,4-dione
(5S)-5-(2-methylpropyl)imidazolidine-2,4-dione
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9.8% of the activity with (5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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r
(5S)-5-(4-hydroxybenzyl)imidazolidine-2,4-dione
(5R)-5-(4-hydroxybenzyl)imidazolidine-2,4-dione
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76.7% of the activity with (5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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r
(5S)-5-benzylimidazolidine-2,4-dione
(5R)-5-benzylimidazolidine-2,4-dione
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62.7% of the activity with (5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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r
(5S)-5-[2-(methylsulfanyl)ethyl]imidazolidine-2,4-dione
(5R)-5-[2-(methylsulfanyl)ethyl]imidazolidine-2,4-dione
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20.4% of the activity with (5S)-5-(1H-indol-2-ylmethyl)imidazolidine-2,4-dione
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D-5-isobutylhydantoin
L-5-isobutylhydantoin
D-5-methylhydantoin
L-5-methylhydantoin
D-benzylhydantoin
L-benzylhydantoin
D-benzylhydantoin
R-benzylhydantoin
D-isobutylhydantoin
L-isobutylhydantoin
L-5-(2-methylthioethyl)hydantoin
D-5-(2-methylthioethyl)hydantoin
L-5-methylhydantoin
D-5-methylhydantoin
L-5-methylthioethylhydantoin
D-5-methylthioethylhydantoin
L-benzylhydantoin
D-benzylhydantoin
L-ethylhydantoin
D-ethylhydantoin
L-isobutylhydantoin
D-isobutylhydantoin
L-isopropylhydantoin
D-isopropylhydantoin
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additional information
?
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D-5-isobutylhydantoin
L-5-isobutylhydantoin
complete racemization
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r
D-5-isobutylhydantoin
L-5-isobutylhydantoin
complete racemization
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r
D-5-methylhydantoin
L-5-methylhydantoin
complete racemization
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r
D-5-methylhydantoin
L-5-methylhydantoin
complete racemization
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r
D-benzylhydantoin
L-benzylhydantoin
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r
D-benzylhydantoin
L-benzylhydantoin
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r
D-benzylhydantoin
R-benzylhydantoin
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final molecular ratio between the isomers is 1:1. Initial specific acitivity with D-benzylhydantoin is 79 U/mg, with L-benzymhydantoin is 100 U/mg
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r
D-benzylhydantoin
R-benzylhydantoin
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final molecular ratio between the isomers is 1:1. Initial specific acitivity with D-benzylhydantoin is 79 U/mg, with L-benzymhydantoin is 100 U/mg
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r
D-isobutylhydantoin
L-isobutylhydantoin
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r
D-isobutylhydantoin
L-isobutylhydantoin
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r
L-5-(2-methylthioethyl)hydantoin
D-5-(2-methylthioethyl)hydantoin
complete racemization
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r
L-5-(2-methylthioethyl)hydantoin
D-5-(2-methylthioethyl)hydantoin
complete racemization
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r
L-5-methylhydantoin
D-5-methylhydantoin
about 50% racemization
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r
L-5-methylhydantoin
D-5-methylhydantoin
about 50% racemization
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r
L-5-methylthioethylhydantoin
D-5-methylthioethylhydantoin
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-
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r
L-5-methylthioethylhydantoin
D-5-methylthioethylhydantoin
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-
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r
L-5-methylthioethylhydantoin
D-5-methylthioethylhydantoin
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r
L-benzylhydantoin
D-benzylhydantoin
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slow racemization
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r
L-benzylhydantoin
D-benzylhydantoin
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slow racemization
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r
L-benzylhydantoin
D-benzylhydantoin
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final molecular ratio between the isomers is 1:1. Initial specific acitivity with D-benzylhydantoin is 79 U/mg, with L-benzymhydantoin is 100 U/mg
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r
L-benzylhydantoin
D-benzylhydantoin
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final molecular ratio between the isomers is 1:1. Initial specific acitivity with D-benzylhydantoin is 79 U/mg, with L-benzymhydantoin is 100 U/mg
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L-benzylhydantoin
D-benzylhydantoin
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r
L-benzylhydantoin
D-benzylhydantoin
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L-ethylhydantoin
D-ethylhydantoin
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r
L-ethylhydantoin
D-ethylhydantoin
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r
L-ethylhydantoin
D-ethylhydantoin
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r
L-ethylhydantoin
D-ethylhydantoin
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r
L-isobutylhydantoin
D-isobutylhydantoin
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r
L-isobutylhydantoin
D-isobutylhydantoin
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r
L-isobutylhydantoin
D-isobutylhydantoin
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L-isobutylhydantoin
D-isobutylhydantoin
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additional information
?
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preference for hydantoins with short rather than long aliphatic side chains or hydantoins with aromatic rings
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?
additional information
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preference for hydantoins with short rather than long aliphatic side chains or hydantoins with aromatic rings
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?
additional information
?
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preference for hydantoins with short rather than long aliphatic side chains or hydantoins with aromatic rings
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?
additional information
?
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preference for hydantoins with short rather than long aliphatic side chains or hydantoins with aromatic rings
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?
additional information
?
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no substrate: DL-5-isopropylhydantoin
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?
additional information
?
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no substrate: DL-5-isopropylhydantoin
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?
additional information
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no substrate: DL-5-isopropylhydantoin
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?
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synthesis
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enzymatic production of D-amino acids via a combination of hydantoin hydrolysis and hydantoin racemization. The D-forms of amino acids D-phenylalanine, D-tyrosine, D-tryptophan, O-benzyl-D-serine, D-valine, D-norvaline, D-leucine and D-norleucine can efficiently be converted from the corresponding DL-5-monosubtituted hydantoin compounds
synthesis
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reaction system for the production of D-amino acids from D,L-5-monosubstituted hydantoins based on recombinant Escherichia coli whole cell biocatalysts containing separately expressed D-hydantoinase, D-carbamoylase, and hydantoin recemase. The system shows high substrate specificity and is effective toward both aliphatic and aromatic D,L-5-monosubstituted hydantoins. At pH 8 and 50°C, 100% conversion of D,L-5-(2-methylthioethyl)-hydantoin (15 mM) into D-methionine is obtained in 30 min
synthesis
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stereospecific production of L-amino acids from the corresponding DL-5-substituted hydantoins. DL-5-substituted hydantoins are converted exclusively to the L-forms of the corresponding N-carbamyl-amino acids by hydantoinase in combination with hydantoin racemase. The N-carbamyl-l-amino acids are then converted to L-amino acids by N-carbamyl-L-amino acid amidohydrolase
synthesis
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stereospecific production of L-amino acids from the corresponding DL-5-substituted hydantoins. DL-5-substituted hydantoins are converted exclusively to the L-forms of the corresponding N-carbamyl-amino acids by hydantoinase in combination with hydantoin racemase. The N-carbamyl-l-amino acids are then converted to L-amino acids by N-carbamyl-L-amino acid amidohydrolase
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synthesis
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enzymatic production of D-amino acids via a combination of hydantoin hydrolysis and hydantoin racemization. The D-forms of amino acids D-phenylalanine, D-tyrosine, D-tryptophan, O-benzyl-D-serine, D-valine, D-norvaline, D-leucine and D-norleucine can efficiently be converted from the corresponding DL-5-monosubtituted hydantoin compounds
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Ishikawa, T.; Watabe, K.; Mukohara, Y.; Nakamura, H.
Mechanism of stereospecific conversion of DL-5-substituted hydantoins to the corresponding L-amino acids by Pseudomonas sp. strain NS671
Biosci. Biotechnol. Biochem.
61
185-187
1997
Pseudomonas sp., Pseudomonas sp. NS671
brenda
Nozaki, H.; Takenaka, Y.; Kira, I.; Watanabe, K.; Yokozeki, K.
D-Amino acid production by E. coli co-expressed three genes encoding hydantoin racemase, D-hydantoinase and N-carbamoyl-D-amino acid amidohydrolase
J. Mol. Catal. B
32
213-218
2005
Microbacterium liquefaciens, Microbacterium liquefaciens AJ3912
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brenda
Martinez-Rodriguez, S.; Gonzalez-Ramirez, L.A.; Clemente-Jimenez, J.M.; Rodriguez-Vico, F.; Las Heras-Vazquez, F.J.; Gavira, J.A.; Garcia-Ruiz, J.M.
Crystallization and preliminary crystallographic studies of an active-site mutant hydantoin racemase from Sinorhizobium meliloti CECT 4114
Acta Crystallogr. Sect. F
F64
50-53
2008
Sinorhizobium meliloti, Sinorhizobium meliloti CECT 4114
brenda
Pietzsch, M.; Syldatk, C.; Wagner, F.
A new racemase for 5-monosubstituted hydantoins
Ann. N. Y. Acad. Sci.
672
478-483
1992
Arthrobacter sp.
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brenda
Martinez-Rodriguez, S.; Las Heras-Vazquez, F.J.; Mingorance-Cazorla, L.; Clemente-Jimenez, J.M.; Rodriguez-Vico, F.
Molecular cloning, purification, and biochemical characterization of hydantoin racemase from the legume symbiont Sinorhizobium meliloti CECT 4114
Appl. Environ. Microbiol.
70
625-630
2004
Sinorhizobium meliloti, Sinorhizobium meliloti CECT 4114
brenda
Las Heras-Vazquez, F.J.; Martinez-Rodriguez, S.; Mingorance-Cazorla, L.; Clemente-Jimenez, J.M.; Rodriguez-Vico, F.
Overexpression and characterization of hydantoin racemase from Agrobacterium tumefaciens C58
Biochem. Biophys. Res. Commun.
303
541-547
2003
Agrobacterium tumefaciens, Agrobacterium tumefaciens C58 / ATCC 33970
brenda
Andujar-Sanchez, M.; Martinez-Rodriguez, S.; Heras-Vazquez, F.J.; Clemente-Jimenez, J.M.; Rodriguez-Vico, F.; Jara-Perez, V.
Binding studies of hydantoin racemase from Sinorhizobium meliloti by calorimetric and fluorescence analysis
Biochim. Biophys. Acta
1764
292-298
2006
Sinorhizobium meliloti
brenda
Martinez-Rodriguez, S.; Las Heras-Vazquez, F.J.; Clemente-Jimenez, J.M.; Rodriguez-Vico, F.
Biochemical characterization of a novel hydantoin racemase from Agrobacterium tumefaciens C58
Biochimie
86
77-81
2004
Agrobacterium tumefaciens, Agrobacterium tumefaciens C58 / ATCC 33970
brenda
Suzuki, S.; Onishi, N.; Yokozeki, K.
Purification and characterization of hydantoin racemase from Microbacterium liquefaciens AJ 3912
Biosci. Biotechnol. Biochem.
69
530-536
2005
Microbacterium liquefaciens, Microbacterium liquefaciens AJ 3912
brenda
Martinez-Rodriguez, S.; Las Heras-Vazquez, F.J.; Clemente-Jimenez, J.M.; Mingorance-Cazorla, L.; Rodriguez-Vico, F.
Complete conversion of D,L-5-monosubstituted hydantoins with a low velocity of chemical racemization into D-amino acids using whole cells of recombinant Escherichia coli
Biotechnol. Prog.
18
1201-1206
2002
Agrobacterium tumefaciens
brenda
Watabe, K.; Ishikawa, T.; Mukohara, Y.; Nakamura, H.
Purification and characterization of the hydantoin racemase of Pseudomonas sp. strain NS671 expressed in Escherichia coli
J. Bacteriol.
174
7989-7995
1992
Pseudomonas sp. (Q00924), Pseudomonas sp., Pseudomonas sp. NS671 (Q00924)
brenda
Martinez-Rodriguez, S.; Andujar-Sanchez, M.; Neira, J.L.; Clemente-Jimenez, J.M.; Jara-Perez, V.; Rodriguez-Vico, F.; Las Heras-Vazquez, F.J.
Site-directed mutagenesis indicates an important role of cysteines 76 and 181 in the catalysis of hydantoin racemase from Sinorhizobium meliloti
Protein Sci.
15
2729-2738
2006
Sinorhizobium meliloti
brenda