KEGG   ENZYME: 1.14.13.187Help
Entry
EC 1.14.13.187              Enzyme                                 

Name
L-evernosamine nitrososynthase
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
dTDP-beta-L-evernosamine,NADPH:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
dTDP-beta-L-evernosamine + 2 NADPH + 2 H+ + 2 O2 = dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + 2 NADP+ + 3 H2O (overall reaction) [RN:R10664];
(1a) dTDP-beta-L-evernosamine + NADPH + H+ + O2 = dTDP-N-hydroxy-beta-L-evernosamine + NADP+ + H2O [RN:R10662];
(1b) dTDP-N-hydroxy-beta-L-evernosamine + NADPH + H+ + O2 = dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose + NADP+ + 2 H2O [RN:R10663]
Reaction(KEGG)
Substrate
dTDP-beta-L-evernosamine [CPD:C20765];
NADPH [CPD:C00005];
H+ [CPD:C00080];
O2 [CPD:C00007];
dTDP-N-hydroxy-beta-L-evernosamine [CPD:C20766]
Product
dTDP-2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitroso-beta-L-arabino-hexopyranose [CPD:C20767];
NADP+ [CPD:C00006];
H2O [CPD:C00001];
dTDP-N-hydroxy-beta-L-evernosamine [CPD:C20766]
Comment
Requires FAD. Isolated from the bacterium Micromonospora carbonacea var. africana. The nitroso group is probably spontaneously oxidized to a nitro group giving dTDP-beta-L-evernitrose, which is involved in the biosynthesis of the antibiotic everninomycin. The reaction was studied using dTDP-beta-L-4-epi-vancosamine (dTDP-4-O-desmethyl-beta-L-evernitrosamine).
History
EC 1.14.13.187 created 2014
Reference
1  [PMID:18983146]
  Authors
Hu Y, Al-Mestarihi A, Grimes CL, Kahne D, Bachmann BO
  Title
A unifying nitrososynthase involved in nitrosugar biosynthesis.
  Journal
J. Am. Chem. Soc. 130 (2008) 15756-7.
Reference
2  [PMID:20866105]
  Authors
Vey JL, Al-Mestarihi A, Hu Y, Funk MA, Bachmann BO, Iverson TM
  Title
Structure and mechanism of ORF36, an amino sugar oxidizing enzyme in everninomicin biosynthesis .
  Journal
Biochemistry. 49 (2010) 9306-17.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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