KEGG   ORTHOLOGY: K15972Help
Entry
K15972                      KO                                     

Name
tcmG, elmG
Definition
tetracenomycin A2 monooxygenase-dioxygenase [EC:1.14.13.200]
Pathway
ko01057  Biosynthesis of type II polyketide products
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00783  Tetracenomycin C/8-demethyltetracenomycin C biosynthesis, tetracenomycin F2 => tetracenomycin C/8-demethyltetracenomycin C
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01057 Biosynthesis of type II polyketide products
    K15972  tcmG, elmG; tetracenomycin A2 monooxygenase-dioxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.13  With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.13.200  tetracenomycin A2 monooxygenase-dioxygenase
     K15972  tcmG, elmG; tetracenomycin A2 monooxygenase-dioxygenase
BRITE hierarchy
Other DBs
RN: R06704 R10954
COG: COG0654
Genes
SGU: SGLAU_26335(tcmG)
SLD: T261_0037
SRO: Sros_4156
AMD: AMED_5441
AMN: RAM_27735
AMM: AMES_5376
AMZ: B737_5376
AG: CAP12596(elmG)
TaxonomyKoalaUniProt
Reference
PMID:8509339
  Authors
Decker H, Motamedi H, Hutchinson CR
  Title
Nucleotide sequences and heterologous expression of tcmG and tcmP, biosynthetic genes for tetracenomycin C in Streptomyces glaucescens.
  Journal
J Bacteriol 175:3876-86 (1993)
DOI:10.1128/JB.175.12.3876-3886.1993
  Sequence
Reference
  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
  Authors
Rafanan ER Jr, Le L, Zhao L, Decker H, Shen B
  Title
Cloning, sequencing, and heterologous expression of the elmGHIJ genes involved in the biosynthesis of the polyketide antibiotic elloramycin from Streptomyces olivaceus Tu2353.
  Journal
J Nat Prod 64:444-9 (2001)
DOI:10.1021/np010007+
  Sequence

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

KEGG   REACTION: R10954Help
Entry
R10954                      Reaction                               

Name
tetracenomycin-B2,NADPH:oxygen oxidoreductase (8-demethyltetracenomycin-C-forming)
Definition
Tetracenomycin B2 + 2 Oxygen + H2O + 2 NADPH + 2 H+ <=> 8-Demethyltetracenomycin C + 2 NADP+ + 2 H2O
Equation
C12378 + 2 C00007 + C00001 + 2 C00005 + 2 C00080 <=> C12379 + 2 C00006 + 2 C00001
Reaction class
RC00001  C00005_C00006
RC02681  C12378_C12379
Enzyme
Pathway
rn01057  Biosynthesis of type II polyketide products
rn01100  Metabolic pathways
rn01130  Biosynthesis of antibiotics
Module
M00783  Tetracenomycin C/8-demethyltetracenomycin C biosynthesis, tetracenomycin F2 => tetracenomycin C/8-demethyltetracenomycin C
Orthology
K15972  tetracenomycin A2 monooxygenase-dioxygenase [EC:1.14.13.200]

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