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.
The enzyme appears in viruses and cellular organisms
reaction proceeds via a monooxygenase-dioxygenase mechanism, deriving the 4- and 12a-OH groups of tetracenomycin C from two molecules of O2 and the 4a-OH group of etracenomycin C from a molecule of H2O
reaction proceeds via a monooxygenase-dioxygenase mechanism, deriving the 4- and 12a-OH groups of tetracenomycin C from two molecules of O2 and the 4a-OH group of etracenomycin C from a molecule of H2O
reaction proceeds via a monooxygenase-dioxygenase mechanism, deriving the 4- and 12a-OH groups of tetracenomycin C from two molecules of O2 and the 4a-OH group of etracenomycin C from a molecule of H2O
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SYSTEMATIC NAME
IUBMB Comments
tetracenomycin A2,NAD(P)H:O2 oxidoreductase (tetracenomycin C forming)
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.
Substrates: tetracenomycin A2 i.e. methyl 10,12-dihydroxy-3,8-dimethoxy-1-methyl-6,11-dioxo-6,11-dihydrotetracene-2-carboxylate. The enzyme prefers NADPH over NADH as an electron donor Products: tetracenomycin C = methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-3,8-dimethoxy-1-methyl-6,10,11-trioxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
Substrates: tetracenomycin A2 i.e. methyl 10,12-dihydroxy-3,8-dimethoxy-1-methyl-6,11-dioxo-6,11-dihydrotetracene-2-carboxylate. The enzyme prefers NADPH over NADH as an electron donor Products: tetracenomycin C = methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-3,8-dimethoxy-1-methyl-6,10,11-trioxo-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
enzyme is responsible for the hydroxylation of tetracenomycin A2 at positions C-4, C-4a, and C-12a to give tetracenomycin C, i.e. the final step in tetracenomycin C biosynthesis
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
protein crystallizes in two different space groups, both with six monomers per asymmetric unit, resulting in large unit-cell parameters. Data from both the hexagonal and tetragonal crystal forms to 4.5 and 4.2 A resolution, respectively
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
Rafanan, E.R.; Le, L.; Zhao, L.; Decker, H.; Shen, B.
Cloning, sequencing, and heterologous expression of the elmGHIJ genes involved in the biosynthesis of the polyketide antibiotic elloramycin from Streptomyces olivaceus Tue2353
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