KEGG   ENZYME: 1.14.13.200Help
Entry
EC 1.14.13.200              Enzyme                                 

Name
tetracenomycin A2 monooxygenase-dioxygenase;
TcmG;
ElmG;
tetracenomycin A2,NAD(P)H:O2 oxidoreductase (tetracenomycin C forming)
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
tetracenomycin A2,NAD(P)H:oxygen oxidoreductase (tetracenomycin C forming)
Reaction(IUBMB)
tetracenomycin A2 + 2 O2 + 2 NAD(P)H + 2 H+ = tetracenomycin C + 2 NAD(P)+ + H2O [RN:R06704]
Reaction(KEGG)
R06704;
(other) R10954
Show
Substrate
tetracenomycin A2 [CPD:C12371];
O2 [CPD:C00007];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080]
Product
tetracenomycin C [CPD:C06801];
NAD+ [CPD:C00003];
NADP+ [CPD:C00006];
H2O [CPD:C00001]
Comment
Isolated from the bacterium Streptomyces glaucescens. The enzyme was also isolated from the bacterium Streptomyces olivaceus, where it acts on 8-demethyltetracenomycin A2 (tetracenomycin B2) as part of elloramycin biosynthesis. The reaction involves a monooxygenase reaction which is followed by a dioxygenase reaction giving a gem-diol and an epoxide. Water opens the epoxide giving two hydroxy groups. The gem-diol eliminates water to give a ketone which is then reduced to a hydroxy group.
History
EC 1.14.13.200 created 2014
Pathway
ec01057  Biosynthesis of type II polyketide products
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
Orthology
K15972  tetracenomycin A2 monooxygenase-dioxygenase
Genes
SGU: SGLAU_26335(tcmG)
SLD: T261_0037
SRO: Sros_4156
AMD: AMED_5441
AMN: RAM_27735
AMM: AMES_5376
AMZ: B737_5376
Taxonomy
Reference
1  [PMID:7982994]
  Authors
Shen B, Hutchinson CR
  Title
Triple hydroxylation of tetracenomycin A2 to tetracenomycin C in Streptomyces glaucescens. Overexpression of the tcmG gene in Streptomyces lividans and characterization of the tetracenomycin A2 oxygenase.
  Journal
J Biol Chem 269:30726-33 (1994)
  Sequence
Reference
2  [PMID:11009387]
  Authors
Rafanan ER Jr, Hutchinson CR, Shen B.
  Title
Triple hydroxylation of tetracenomycin A2 to tetracenomycin C involving two molecules of O(2) and one molecule of H(2)O.
  Journal
Org Lett 2:3225-7 (2000)
DOI:10.1021/ol0002267
Reference
3  [PMID:11092935]
  Authors
Beynon J, Rafanan ER Jr, Shen B, Fisher AJ
  Title
Crystallization and preliminary X-ray analysis of tetracenomycin A2 oxygenase: a  flavoprotein hydroxylase involved in polyketide biosynthesis.
  Journal
Acta Crystallogr D Biol Crystallogr 56:1647-51 (2000)
DOI:10.1107/S0907444900012695
Other DBs
ExplorEnz - The Enzyme Database: 1.14.13.200
IUBMB Enzyme Nomenclature: 1.14.13.200
ExPASy - ENZYME nomenclature database: 1.14.13.200
BRENDA, the Enzyme Database: 1.14.13.200

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