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

tetracenomycin A2,NAD(P)H:oxygen oxidoreductase (tetracenomycin C forming)

tetracenomycin A2 + 2 O2 + 2 NAD(P)H + 2 H+ = tetracenomycin C + 2 NAD(P)+ + H2O [RN:R06704]

R06704;
(other) R10954

tetracenomycin A2 [CPD:C12371];
O2 [CPD:C00007];
NADH [CPD:C00004];
NADPH [CPD:C00005];
H+ [CPD:C00080]

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.

EC 1.14.13.200 created 2014

1  [PMID:7982994]

Shen B, Hutchinson CR

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.

J Biol Chem 269:30726-33 (1994)

[sgu:SGLAU_26335]

2  [PMID:11009387]

Rafanan ER Jr, Hutchinson CR, Shen B.

Triple hydroxylation of tetracenomycin A2 to tetracenomycin C involving two molecules of O(2) and one molecule of H(2)O.

Org Lett 2:3225-7 (2000)
DOI:10.1021/ol0002267

3  [PMID:11092935]

Beynon J, Rafanan ER Jr, Shen B, Fisher AJ

Crystallization and preliminary X-ray analysis of tetracenomycin A2 oxygenase: a  flavoprotein hydroxylase involved in polyketide biosynthesis.

Acta Crystallogr D Biol Crystallogr 56:1647-51 (2000)
DOI:10.1107/S0907444900012695