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Information on EC 5.1.1.15 - 2-aminohexano-6-lactam racemase
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EC Tree
5.1.1.15 2-aminohexano-6-lactam racemaseIUBMB Comments
Contains pyridoxal 5'-phosphate. Also racemises 2-aminopentano-5-lactam (alpha-amino-delta-valerolactam) and 2-amino-4-thiahexano-6-lactam (where S replaces CH2 of C-4). It does not catalyse the racemisation of alpha-amino acids but has some transaminase activity with them.
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Word Map
- 5.1.1.15
- synthesis
- amide
-
racemization
- d-aminopeptidase
- 5'-phosphate
-
ochrobactrum
- pyridoxal
- anthropi
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
alpha-amino-epsilon-caprolactam racemase, aminocaprolactam racemase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
ACL racemase
ACLR
alpha-Amino-delta-valerolactam racemase
-
-
-
-
alpha-Amino-epsilon-caprolactam racemase
Aminocaprolactam racemase
-
-
-
-
moe
Racemase, alpha-amino-epsilon-caprolactam
-
-
-
-
Racemase, alpha-amino-epsilon-caprolactam (Achromobacter obae reduced)
-
-
-
-
additional information
ACL racemase
-
-
-
-
alpha-Amino-epsilon-caprolactam racemase
-
-
-
-
alpha-Amino-epsilon-caprolactam racemase
Brucella anthropi ATCC 49188 / DSM 6882 / JCM 21032 / NBRC 15819 / NCTC 12168
-
-
additional information
Brucella anthropi ATCC 49188 / DSM 6882 / JCM 21032 / NBRC 15819 / NCTC 12168
cf. EC 5.1.1.10
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-2-aminohexano-6-lactam = (R)-2-aminohexano-6-lactam
single base mechanism
-
(S)-2-aminohexano-6-lactam = (R)-2-aminohexano-6-lactam
D- and L-amino acids are produced from L- and D-amino acid amides by D-aminopeptidase from Ochrobactrum anthropi C1-38 and L-amino acid amidase from Pseudomonas azotoformans IAM 1603, respectively, in the presence of alpha-amino-epsilon-caprolactam racemase from Achromobacter obae. Substrate: L-alanine amide, product: D-alanine (100% yield), substrate: L-2-aminobutyric amide, product: D-2-aminobutyric acid (100% yield), substrate: L-serine amide, product: D-serine (94% yield), substrate: L-methionine amide, product: D-methionine (100% yield), substrate: D-alanine amide, product: L-alanine (100% yield), substrate: D-leucine amide, product: L-leucine (100% yield), substrate: D-methionine amide, product: L-methionine (100% yield)
-
(S)-2-aminohexano-6-lactam = (R)-2-aminohexano-6-lactam
the racemization of ACL racemase proceeds via a two-base mechanism
(S)-2-aminohexano-6-lactam = (R)-2-aminohexano-6-lactam
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
isomerization
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
2-aminohexano-6-lactam racemase
Contains pyridoxal 5'-phosphate. Also racemises 2-aminopentano-5-lactam (alpha-amino-delta-valerolactam) and 2-amino-4-thiahexano-6-lactam (where S replaces CH2 of C-4). It does not catalyse the racemisation of alpha-amino acids but has some transaminase activity with them.
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CAS REGISTRY NUMBER
COMMENTARY
120669-89-8
racemase, alpha-amino-epsilon-caprolactam (Achromobacter obae reduced)
52652-64-9
-
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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
D-2-amino-delta-valerolactam
L-2-amino-delta-valerolactam
-
best substrate
-
-
r
D-2-amino-omega-octalactam
L-2-amino-omega-octalactam
-
1.78% activity compared to D-2-aminohexano-6-lactam
-
-
r
D-2-aminobutyric acid amide
L-2-aminobutyric acid amide
-
0.19% activity compared to D-2-aminohexano-6-lactam
-
-
r
D-alanine amide
L-alanine amide
-
2.12% activity compared to D-2-aminohexano-6-lactam
-
-
r
L-2-amino-delta-valerolactam
D-2-amino-delta-valerolactam
-
17.2% activity compared to D-2-aminohexano-6-lactam
-
-
r
L-2-amino-omega-octalactam
D-2-amino-omega-octalactam
-
1.41% activity compared to D-2-aminohexano-6-lactam
-
-
r
L-alpha-Amino-beta-thio-epsilon-caprolactam
D-alpha-Amino-beta-thio-epsilon-caprolactam
-
racemized more than 3times faster and binds about 4fold stronger to the enzyme than L-alpha-amino-epsilon-caprolactam
-
-
?
L-alpha-Amino-delta-valerolactam
D-alpha-Amino-delta-valerolactam
-
-
-
?
D-2-aminohexano-6-lactam
L-2-aminohexano-6-lactam
preferred substrate
-
-
r
D-2-aminohexano-6-lactam
L-2-aminohexano-6-lactam
-
preferred substrate
-
-
r
D-2-aminohexano-6-lactam
L-2-aminohexano-6-lactam
-
-
-
r
D-2-aminohexano-6-lactam
L-2-aminohexano-6-lactam
-
-
-
r
L-2-aminobutyric acid amide
D-2-aminobutyric acid amide
-
0.08% activity compared to D-2-aminohexano-6-lactam
-
-
r
L-2-aminohexano-6-lactam
D-2-aminohexano-6-lactam
high activity
-
-
r
L-2-aminohexano-6-lactam
D-2-aminohexano-6-lactam
-
-
-
r
L-2-aminohexano-6-lactam
D-2-aminohexano-6-lactam
-
-
-
r
L-alanine amide
D-alanine amide
-
0.77% activity compared to D-2-aminohexano-6-lactam
-
-
r
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
r
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
r
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
r
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
r
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
?
additional information
?
-
-
the enzyme catalyzes alpha-proton exchange of the substrate with deuterium during racemization in deuterium oxide
-
-
?
additional information
?
-
-
no racemization activity is observed with dipeptides or amino acid derivatives, such as L-Ala-D-Ala, D-Ala-L-Ala, L-alanylglycine, L-phenylglycine, or L-alanine methylester
-
-
?
additional information
?
-
The enzyme acts on a broad range of amino acid amides, particularly unbranched amino acid amides including L-alanine amide and L-serine amide. No activity with L-tyrosine amide
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-leucine amide, and L-phenylglycine amide, and not active on L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene Oant_4493 is an aminotransferase class-III (UniProt ID A6X7I5), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene Oant_4493 is an aminotransferase class-III (UniProt ID A6X7I5), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-tyrosine amide, and L-phenylglycine amide, and not active on L-leucine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-tyrosine amide, and L-phenylglycine amide, and not active on L-leucine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
Brucella anthropi IA / NCBIMB41129
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
Brucella anthropi IA / NCBIMB41129
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
-
the enzyme encoded by gene CSE45_2055 is a 2,2-dialkylglycine decarboxylase, EC 4.1.1.64 (UniProt ID D0D2T1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene CSE45_2055 is a 2,2-dialkylglycine decarboxylase, EC 4.1.1.64 (UniProt ID D0D2T1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
The enzyme acts on a broad range of amino acid amides, particularly unbranched amino acid amides including L-alanine amide and L-serine amide. No activity with L-tyrosine amide
-
-
?
additional information
?
-
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-leucine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
-
the enzyme acts on 2-aminohexano-6-lactam and 2-amino acid amides, the enzyme prefers the D-enantiomers as substrates
-
-
?
additional information
?
-
-
the enzyme encoded by gene CQ758817 shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-phenylglycine amide, L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme encoded by gene JNB_04915 is a Putative aminotransferase protein (UniProt ID A3TM80), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme encoded by gene Mesop_2670 is an aminotransferase class-III (UniProt ID F7Y223), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-phenylglycine amide, L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme encoded by gene Mvan_2918 is an aminotransferase (EC 2.6.1, UniProt ID A1T974), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, L-serine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme encoded by gene Smed_5339 is an aminotransferase class-III (UniProt ID A6UKD1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-tyrosine amide, and L-phenylglycine amide, and not active on L-leucine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme encoded by gene SM0020_01805 is an acetylornithine transaminase (UniProt ID H0FT96), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SM0020_01805 is an acetylornithine transaminase (UniProt ID H0FT96), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SMc02413 is a class-III pyridoxal-phosphate-dependent aminotransferase family protein, UniProt ID Q92MM4,that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SMc02413 is a class-III pyridoxal-phosphate-dependent aminotransferase family protein, UniProt ID Q92MM4,that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-leucine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-phenylglycine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-leucine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, L-phenylglycine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
additional information
?
-
the enzyme is also active on L-alanine, L-alanine amide, L-serine amide, L-valine amide, L-methionine amide, L-phenylalanine amide, and L-phenylglycine amide, and not active on L-leucine amide, and L-tyrosine amide, cf. EC 5.1.1.10
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL 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
L-alpha-Amino-epsilon-caprolactam
D-alpha-Amino-epsilon-caprolactam
-
-
-
r
additional information
?
-
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene Oant_4493 is an aminotransferase class-III (UniProt ID A6X7I5), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene Oant_4493 is an aminotransferase class-III (UniProt ID A6X7I5), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
Brucella anthropi IA / NCBIMB41129
-
the enzyme encoded by gene ABI14443 is an amino acid amide racemase (UniProt ID Q06K28), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene CSE45_2055 is a 2,2-dialkylglycine decarboxylase, EC 4.1.1.64 (UniProt ID D0D2T1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene CSE45_2055 is a 2,2-dialkylglycine decarboxylase, EC 4.1.1.64 (UniProt ID D0D2T1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
-
the enzyme encoded by gene CQ758817 shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene JNB_04915 is a Putative aminotransferase protein (UniProt ID A3TM80), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene Mesop_2670 is an aminotransferase class-III (UniProt ID F7Y223), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene Mvan_2918 is an aminotransferase (EC 2.6.1, UniProt ID A1T974), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene Smed_5339 is an aminotransferase class-III (UniProt ID A6UKD1), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SM0020_01805 is an acetylornithine transaminase (UniProt ID H0FT96), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SM0020_01805 is an acetylornithine transaminase (UniProt ID H0FT96), that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SMc02413 is a class-III pyridoxal-phosphate-dependent aminotransferase family protein, UniProt ID Q92MM4,that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
additional information
?
-
the enzyme encoded by gene SMc02413 is a class-III pyridoxal-phosphate-dependent aminotransferase family protein, UniProt ID Q92MM4,that shows enhanced alpha-amino-epsilon-caprolactam racemase activity on D- and L-2-aminohexano-6-lactams
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
pyridoxal 5'-phosphate
-
enzyme contains 1 mol of pyridoxal 5'-phosphate per mol of enzyme. Km: 0.00021 mM
pyridoxal 5'-phosphate
PLP, the enzyme is a fold-type I PLP-dependent enzyme
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
L-alpha-Amino-delta-valerolactam
-
inactivation is due to conversion of the enzyme-bound pyridoxal 5'-phosphate into pyridoxamine 5'-phosphate by transamination with L-alpha-amino-delta-valerolactam