KEGG   ENZYME: 1.3.3.19
Entry
EC 1.3.3.19                 Enzyme                                 
Name
N-acyl-aromatic-amino-acid desaturase;
tyzC (gene name);
oxzB (gene name);
trzS (gene name)
Class
Oxidoreductases;
Acting on the CH-CH group of donors;
With oxygen as acceptor
Sysname
N-acyl-aromatic amino acid:oxygen 2-oxidoreductase
Reaction(IUBMB)
(1) an N-acyl-L-tryptophan + O2 = a (2E)-N-acyl-2-dehydrotryptophan + H2O2 [RN:R13709];
(2) an N-acyl-L-tyrosine + O2 = a (2E)-N-acyl-2-dehydrotyrosine + H2O2 [RN:R13708];
(3) an N-acyl-L-phenylalanine + O2 = a (2E)-N-acyl-2-dehydrophenylalanine + H2O2 [RN:R13710]
Reaction(KEGG)
Substrate
N-acyl-L-tryptophan [CPD:C23151];
O2 [CPD:C00007];
N-acyl-L-tyrosine [CPD:C23152];
N-acyl-L-phenylalanine [CPD:C23153]
Product
(2E)-N-acyl-2-dehydrotryptophan [CPD:C23178];
H2O2 [CPD:C00027];
(2E)-N-acyl-2-dehydrotyrosine [CPD:C23177];
(2E)-N-acyl-2-dehydrophenylalanine [CPD:C23179]
Comment
Contains FMN. The enzyme catalyses a step in the biosynthesis of oxazolone compounds (phenazolones, tyrazolones, and tryptazolones), which have been reported from Gram-negative as well as Gram-positive bacteria. The enzyme acts along EC 6.1.3.2, N-acyl-2-dehydroaromatic-amino-acid cyclase, and the order in which the two enzymes act has not been determined conclusively. In some organisms the two enzymes form a fusion protein.
History
EC 1.3.3.19 created 2026
Reference
1  [PMID:34099916]
  Authors
de Rond T, Asay JE, Moore BS.
  Title
Co-occurrence of enzyme domains guides the discovery of an oxazolone synthetase.
  Journal
Nat Chem Biol 17:794-799 (2021)
DOI:10.1038/s41589-021-00808-4
Reference
2  [PMID:37328106]
  Authors
Grigg JC, Copp JN, Krekhno JMC, Liu J, Ibrahimova A, Eltis LD.
  Title
Deciphering the biosynthesis of a novel lipid in Mycobacterium tuberculosis expands the known roles of the nitroreductase superfamily.
  Journal
J Biol Chem 299:104924 (2023)
DOI:10.1016/j.jbc.2023.104924
  Sequence
[mtu:Rv2337c]
Reference
3  [PMID:41429352]
  Authors
Kleetz J, Grigg JC, Hassan AA, Ibtisam A, Copp JN, Lian J, Liu J, Eltis LD.
  Title
The biosynthesis of N-acylated tryptazolone in Mycobacterium tuberculosis and related bacteria.
  Journal
J Biol Chem 302:111079 (2026)
DOI:10.1016/j.jbc.2025.111079
  Sequence
[mtu:Rv1355c]
Other DBs
ExplorEnz - The Enzyme Database: 1.3.3.19
IUBMB Enzyme Nomenclature: 1.3.3.19
ExPASy - ENZYME nomenclature database: 1.3.3.19
BRENDA, the Enzyme Database: 1.3.3.19
LinkDB

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