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ENZYME entry: EC 1.14.13.250

Accepted Name
nitrosourea synthase.
Reaction catalysed
H(+) + N(omega)-methyl-L-arginine + 2 NADH + 3 O2 <=> 3 H2O + N(delta)-hydroxy-N(omega)-methyl-N(omega)-nitroso-L-citrulline + 2 NAD(+)
Comment(s)
  • The enzyme, characterized from the bacterium Streptomyces achromogenes subsp. streptozoticus, catalyzes a complex multi-step reaction during the biosynthesis of the glucosamine-nitrosourea antibiotic streptozotocin.
  • The overall reaction is an oxidative rearrangement of the guanidine group of N(omega)-methyl-L-arginine, generating an N-nitrosourea product.
  • The enzyme hydroxylates its substrate at the N(delta) position, followed by a second hydroxylation at the N(omega)' position. It then catalyzes an oxidative rearrangement to form N(delta)-hydroxy- N(omega)-methyl-N(omega)-nitroso-L-citrulline.
  • This product is unstable, and degrades non-enzymically into nitric oxide and the denitrosated product N(delta)-hydroxy-N(omega)-methyl- L-citrulline.
  • The enzyme contains two active sites, each of which utilizes a different iron-containing cofactor.
Cross-references
BRENDA1.14.13.250
EC2PDB1.14.13.250
ExplorEnz1.14.13.250
PRIAM enzyme-specific profiles1.14.13.250
KEGG Ligand Database for Enzyme Nomenclature1.14.13.250
IUBMB Enzyme Nomenclature1.14.13.250
IntEnz1.14.13.250
MEDLINEFind literature relating to 1.14.13.250
MetaCyc1.14.13.250
Rhea expert-curated reactions1.14.13.250

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