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Information on EC 1.14.13.250 - nitrosourea synthase

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IUBMB Comments
The enzyme, characterized from the bacterium Streptomyces achromogenes subsp. streptozoticus, catalyses 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 Nomega-methyl-L-arginine, generating an N-nitrosourea product. The enzyme hydroxylates its substrate at the Ndelta position, followed by a second hydroxylation at the Nomega' position. It then catalyses an oxidative rearrangement to form Ndelta-hydroxy-Nomega-methyl-Nomega-nitroso-L-citrulline. This product is unstable, and degrades non-enzymically into nitric oxide and the denitrosated product Ndelta-hydroxy-Nomega-methyl-L-citrulline. The enzyme contains two active sites, each of which utilizes a different iron-containing cofactor.
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The expected taxonomic range for this enzyme is: Streptomyces achromogenes subsp. streptozoticus
Reaction Schemes
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Synonyms
StzF, sznF, more
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
Ndelta,Nomega'-dihydroxy-Nomega-methyl-L-arginine + O2 = Ndelta-hydroxy-Nomega-methyl-Nomega-nitroso-L-citrulline + H2O
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1c
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Ndelta-hydroxy-Nomega-methyl-L-arginine + NADH + H+ + O2 = Ndelta,Nomega'-dihydroxy-Nomega-methyl-L-arginine + NAD+ + H2O
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1b
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Nomega-methyl-L-arginine + 2 NADH + 2 H+ + 3 O2 = Ndelta-hydroxy-Nomega-methyl-Nomega-nitroso-L-citrulline + 2 NAD+ + 3 H2O
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overall reaction
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Nomega-methyl-L-arginine + NADH + H+ + O2 = Ndelta-hydroxy-Nomega-methyl-L-arginine + NAD+ + H2O
show the reaction diagram
1a
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PATHWAY SOURCE
PATHWAYS
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