The Enzyme Database

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EC 1.13.12.21     
Accepted name: tetracenomycin-F1 monooxygenase
Reaction: tetracenomycin F1 + O2 = tetracenomycin D3 + H2O
For diagram of tetracenomycin biosynthesis, click here
Glossary: tetracenomycin D3 = 3,8,10,12-tetrahydroxy-1-methyl-6,11-dioxo-6,11-dihydrotetracene-2-carboxylate = 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-6,11-dioxonaphthacene-2-carboxylate
tetracenomycin F1 = 3,8,10,12-tetrahydroxy-1-methyl-11-oxo-6,11-dihydro-2-tetracenecarboxylate = 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-11-oxonaphthacene-2-carboxylate
Other name(s): tcmH (gene name)
Systematic name: tetracenomycin-F1:oxygen C5-monooxygenase
Comments: The enzyme is involved in biosynthesis of the anthracycline antibiotic tetracenomycin C by the bacterium Streptomyces glaucescens.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Shen, B. and Hutchinson, C.R. Tetracenomycin F1 monooxygenase: oxidation of a naphthacenone to a naphthacenequinone in the biosynthesis of tetracenomycin C in Streptomyces glaucescens. Biochemistry 32 (1993) 6656–6663. [PMID: 8329392]
[EC 1.13.12.21 created 2013]
 
 
EC 1.14.13.200     
Accepted name: tetracenomycin A2 monooxygenase-dioxygenase
Reaction: tetracenomycin A2 + 2 O2 + 2 NAD(P)H + 2 H+ = tetracenomycin C + 2 NAD(P)+ + H2O
For diagram of tetracenomycin biosynthesis, click here
Glossary: tetracenomycin A2 = methyl 10,12-dihydroxy-3,8-dimethoxy-1-methyl-6,11-dioxo-6,11-dihydrotetracene-2-carboxylate
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
Other name(s): TcmG; ElmG; tetracenomycin A2,NAD(P)H:O2 oxidoreductase (tetracenomycin C forming)
Systematic name: tetracenomycin A2,NAD(P)H:oxygen oxidoreductase (tetracenomycin-C-forming)
Comments: 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Shen, B. and Hutchinson, C.R. 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 (1994) 30726–30733. [PMID: 7982994]
2.  Rafanan, E.R., Jr., Hutchinson, C.R. and Shen, B. Triple hydroxylation of tetracenomycin A2 to tetracenomycin C involving two molecules of O2 and one molecule of H2O. Org. Lett. 2 (2000) 3225–3227. [DOI] [PMID: 11009387]
3.  Beynon, J., Rafanan, E.R., Jr., Shen, B. and Fisher, A.J. Crystallization and preliminary X-ray analysis of tetracenomycin A2 oxygenase: a flavoprotein hydroxylase involved in polyketide biosynthesis. Acta Crystallogr. D Biol. Crystallogr. 56 (2000) 1647–1651. [PMID: 11092935]
[EC 1.14.13.200 created 2014]
 
 
EC 2.1.1.305     
Accepted name: 8-demethyl-8-α-L-rhamnosyltetracenomycin-C 2′-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 8-demethyl-8-α-L-rhamnosyltetracenomycin C = S-adenosyl-L-homocysteine + 8-demethyl-8-(2-O-methyl-α-L-rhamnosyl)tetracenomycin C
For diagram of elloramycin biosynthesis, click here
Glossary: 8-demethyl-8-α-L-rhamnosyltetracenomycin C = methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-3-α-L-rhamnosyloxy-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
Other name(s): ElmMI
Systematic name: S-adenosyl-L-methionine:8-demethyl-8-α-L-rhamnosyltetracenomycin-C 2′-O-methyltransferase
Comments: The enzyme from the bacterium Streptomyces olivaceus is involved in the biosynthesis of the polyketide elloramycin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Patallo, E.P., Blanco, G., Fischer, C., Brana, A.F., Rohr, J., Mendez, C. and Salas, J.A. Deoxysugar methylation during biosynthesis of the antitumor polyketide elloramycin by Streptomyces olivaceus. Characterization of three methyltransferase genes. J. Biol. Chem. 276 (2001) 18765–18774. [DOI] [PMID: 11376004]
[EC 2.1.1.305 created 2014]
 
 
EC 2.1.1.306     
Accepted name: 8-demethyl-8-(2-methoxy-α-L-rhamnosyl)tetracenomycin-C 3′-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 8-demethyl-8-(2-O-methyl-α-L-rhamnosyl)tetracenomycin C = S-adenosyl-L-homocysteine + 8-demethyl-8-(2,3-di-O-methyl-α-L-rhamnosyl)tetracenomycin C
For diagram of elloramycin biosynthesis, click here
Glossary: 8-demethyl-8-α-L-rhamnosyltetracenomycin C = methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-3-α-L-rhamnosyloxy-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
Other name(s): ElmMII
Systematic name: S-adenosyl-L-methionine:8-demethyl-8-(2-methoxy-α-L-rhamnosyl)tetracenomycin-C 3′-O-methyltransferase
Comments: The enzyme from the bacterium Streptomyces olivaceus is involved in the biosynthesis of the polyketide elloramycin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Patallo, E.P., Blanco, G., Fischer, C., Brana, A.F., Rohr, J., Mendez, C. and Salas, J.A. Deoxysugar methylation during biosynthesis of the antitumor polyketide elloramycin by Streptomyces olivaceus. Characterization of three methyltransferase genes. J. Biol. Chem. 276 (2001) 18765–18774. [DOI] [PMID: 11376004]
[EC 2.1.1.306 created 2014]
 
 
EC 2.1.1.307     
Accepted name: 8-demethyl-8-(2,3-dimethoxy-α-L-rhamnosyl)tetracenomycin-C 4′-O-methyltransferase
Reaction: S-adenosyl-L-methionine + 8-demethyl-8-(2,3-di-O-methyl-α-L-rhamnosyl)tetracenomycin C = S-adenosyl-L-homocysteine + 8-demethyl-8-(2,3,4-tri-O-methyl-α-L-rhamnosyl)tetracenomycin C
For diagram of elloramycin biosynthesis, click here
Glossary: 8-demethyl-8-α-L-rhamnosyltetracenomycin C = methyl (6aR,7S,10aR)-6a,7,10a,12-tetrahydroxy-8-methoxy-1-methyl-6,10,11-trioxo-3-α-L-rhamnosyloxy-6,6a,7,10,10a,11-hexahydrotetracene-2-carboxylate
Other name(s): ElmMIII
Systematic name: S-adenosyl-L-methionine:8-demethyl-8-(2,3-di-O-methoxy-α-L-rhamnosyl)tetracenomycin-C 4′-O-methyltransferase
Comments: The enzyme from the bacterium Streptomyces olivaceus is involved in the biosynthesis of the polyketide elloramycin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Patallo, E.P., Blanco, G., Fischer, C., Brana, A.F., Rohr, J., Mendez, C. and Salas, J.A. Deoxysugar methylation during biosynthesis of the antitumor polyketide elloramycin by Streptomyces olivaceus. Characterization of three methyltransferase genes. J. Biol. Chem. 276 (2001) 18765–18774. [DOI] [PMID: 11376004]
[EC 2.1.1.307 created 2014]
 
 
EC 2.4.1.331     
Accepted name: 8-demethyltetracenomycin C L-rhamnosyltransferase
Reaction: dTDP-β-L-rhamnose + 8-demethyltetracenomycin C = dTDP + 8-demethyl-8-α-L-rhamnosyltetracenomycin C
For diagram of elloramycin biosynthesis, click here
Glossary: dTDP-β-L-rhamnose = dTDP-6-deoxy-β-L-mannose
Other name(s): elmGT
Systematic name: dTDP-β-L-rhamnose:8-demethyltetracenomycin C 3-α-L-rhamnosyltransferase
Comments: Isolated from Streptomyces olivaceus Tü2353. Involved in elloramycin biosynthesis. In vitro it can also utilize other 6-deoxy D- or L-hexoses.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Blanco, G., Patallo, E.P., Brana, A.F., Trefzer, A., Bechthold, A., Rohr, J., Mendez, C. and Salas, J.A. Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin. Chem. Biol. 8 (2001) 253–263. [DOI] [PMID: 11306350]
[EC 2.4.1.331 created 2014]
 
 
EC 4.2.1.154     
Accepted name: tetracenomycin F2 cyclase
Reaction: tetracenomycin F2 = tetracenomycin F1 + H2O
For diagram of tetracenomycin biosynthesis, click here
Glossary: tetracenomycin F1 = 3,8,10,12-tetrahydroxy-1-methyl-11-oxo-6,11-dihydro-2-tetracenecarboxylate = 6,11-dihydro-3,8,10,12-tetrahydroxy-1-methyl-11-oxonaphthacene-2-carboxylate
tetracenomycin F2 = (3E)-4-(3-acetyl-4,5,7-trihydroxy-10-oxo-9,10-dihydroanthracen-2-yl)-3-hydroxybut-3-enoate
Other name(s): tcmI (gene name)
Systematic name: tetracenomycin F2 hydro-lyase (tetracenomycin-F1-forming)
Comments: The enzyme is involved in biosynthesis of the anthracycline antibiotic tetracenomycin C by the bacterium Streptomyces glaucescens.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Shen, B. and Hutchinson, C.R. Tetracenomycin F2 cyclase: intramolecular aldol condensation in the biosynthesis of tetracenomycin C in Streptomyces glaucescens. Biochemistry 32 (1993) 11149–11154. [PMID: 8218177]
2.  Thompson, T.B., Katayama, K., Watanabe, K., Hutchinson, C.R. and Rayment, I. Structural and functional analysis of tetracenomycin F2 cyclase from Streptomyces glaucescens. A type II polyketide cyclase. J. Biol. Chem. 279 (2004) 37956–37963. [DOI] [PMID: 15231835]
[EC 4.2.1.154 created 2014]
 
 


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