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Chemical Compound Review

Tetracenomycin     methyl6a,7,10a,12- tetrahydroxy-3,8...

Synonyms: SureCN6840637, ACMC-20n4zl, CTK0H6212, AC1L2RC9, 5838-Dni, ...
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Disease relevance of Tetracenomycin


High impact information on Tetracenomycin

  • Cloning and heterologous expression of a gene cluster for the biosynthesis of tetracenomycin C, the anthracycline antitumor antibiotic of Streptomyces glaucescens [6].
  • The tcm biosynthetic and resistance genes occur as a single cluster in the S. glaucescens genome and are expressed in heterologous streptomycete hosts like S. lividans, resulting in the overproduction of pigmented intermediates of the tetracenomycin C biosynthetic pathway [6].
  • Through complementation of mutations specifically blocking the biosynthesis of tetracenomycin C by Streptomyces glaucescens and selecting for resistance to tetracenomycin C in Streptomyces lividans, all of the genes for the production of tetracenomycin C were inserted in pIJ702, a high copy-number Streptomyces gene cloning vector [6].
  • Tetracenomycin F2 cyclase (tcmI gene product), catalyzes an aromatic rearrangement in the biosynthetic pathway for tetracenomycin C in Streptomyces glaucescens [7].
  • Unexpectedly, however, when the C-terminal domain of the gris ARO/CYC was expressed in a context where aromatase activity was absent, it could modulate the chain length specificity of the tetracenomycin (tcm) minimal PKS, leading to the formation of a novel 18-carbon product in addition to the expected 20-carbon one [8].

Chemical compound and disease context of Tetracenomycin


Biological context of Tetracenomycin


Gene context of Tetracenomycin

  • Incubations of tetracenomycin ACP (TcmM) with the Escherichia coli FAS ACP (AcpP) unexpectedly revealed that, in addition to the self-malonylation process, TcmM can catalyze the malonylation of AcpP [14].
  • In the absence of alternative acyl donors, ZhuC severely retarded the activity of the tcm minimal PKS [15].
  • The acyl carrier protein (ACP) of the tetracenomycin C polyketide synthase, encoded by the tcmM gene, has been expressed in both Streptomyces glaucescens and Escherichia coli and purified to homogeneity [16].
  • Sequence and transcriptional analysis of the Streptomyces glaucescens tcmAR tetracenomycin C resistance and repressor gene loci [17].
  • The five ORFs show high sequence similarities to ORFs that were previously identified in the granaticin, actinorhodin, tetracenomycin and whiE PKS gene clusters [18].

Analytical, diagnostic and therapeutic context of Tetracenomycin


  1. Enzymatic synthesis of a bacterial polyketide from acetyl and malonyl coenzyme A. Shen, B., Hutchinson, C.R. Science (1993) [Pubmed]
  2. Ability of Streptomyces spp. acyl carrier proteins and coenzyme A analogs to serve as substrates in vitro for E. coli holo-ACP synthase. Gehring, A.M., Lambalot, R.H., Vogel, K.W., Drueckhammer, D.G., Walsh, C.T. Chem. Biol. (1997) [Pubmed]
  3. New agents active against African swine fever virus. Sola, A., Rodríguez, S., Gil-Fernández, C., Alarcón, B., González, M.E., Carrasco, L. Antimicrob. Agents Chemother. (1986) [Pubmed]
  4. 5838-DNI, a deoxyribonuclease inhibitor produced by Streptomyces sp. strain no. A-5838. Uyeda, M., Nagao, K., Kido, Y., Suzuki, K., Hara, Y., Yamamura, R. J. Enzym. Inhib. (1992) [Pubmed]
  5. Screening for new compounds with antiherpes activity. Alarcón, B., Lacal, J.C., Fernández-Sousa, J.M., Carrasco, L. Antiviral Res. (1984) [Pubmed]
  6. Cloning and heterologous expression of a gene cluster for the biosynthesis of tetracenomycin C, the anthracycline antitumor antibiotic of Streptomyces glaucescens. Motamedi, H., Hutchinson, C.R. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  7. Structural and functional analysis of tetracenomycin F2 cyclase from Streptomyces glaucescens. A type II polyketide cyclase. Thompson, T.B., Katayama, K., Watanabe, K., Hutchinson, C.R., Rayment, I. J. Biol. Chem. (2004) [Pubmed]
  8. Domain analysis of the molecular recognition features of aromatic polyketide synthase subunits. Zawada, R.J., Khosla, C. J. Biol. Chem. (1997) [Pubmed]
  9. Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin. Blanco, G., Patallo, E.P., Braña, A.F., Trefzer, A., Bechthold, A., Rohr, J., Méndez, C., Salas, J.A. Chem. Biol. (2001) [Pubmed]
  10. Tetracenomycin F1 monooxygenase: oxidation of a naphthacenone to a naphthacenequinone in the biosynthesis of tetracenomycin C in Streptomyces glaucescens. Shen, B., Hutchinson, C.R. Biochemistry (1993) [Pubmed]
  11. 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. Shen, B., Hutchinson, C.R. J. Biol. Chem. (1994) [Pubmed]
  12. Deciphering the biosynthetic origin of the aglycone of the aureolic acid group of anti-tumor agents. Blanco, G., Fu, H., Mendez, C., Khosla, C., Salas, J.A. Chem. Biol. (1996) [Pubmed]
  13. The tcmVI region of the tetracenomycin C biosynthetic gene cluster of Streptomyces glaucescens encodes the tetracenomycin F1 monooxygenase, tetracenomycin F2 cyclase, and, most likely, a second cyclase. Summers, R.G., Wendt-Pienkowski, E., Motamedi, H., Hutchinson, C.R. J. Bacteriol. (1993) [Pubmed]
  14. Polyketide synthase acyl carrier protein (ACP) as a substrate and a catalyst for malonyl ACP biosynthesis. Zhou, P., Florova, G., Reynolds, K.A. Chem. Biol. (1999) [Pubmed]
  15. The acyltransferase homologue from the initiation module of the R1128 polyketide synthase is an acyl-ACP thioesterase that edits acetyl primer units. Tang, Y., Koppisch, A.T., Khosla, C. Biochemistry (2004) [Pubmed]
  16. Purification and characterization of the acyl carrier protein of the Streptomyces glaucescens tetracenomycin C polyketide synthase. Shen, B., Summers, R.G., Gramajo, H., Bibb, M.J., Hutchinson, C.R. J. Bacteriol. (1992) [Pubmed]
  17. Sequence and transcriptional analysis of the Streptomyces glaucescens tcmAR tetracenomycin C resistance and repressor gene loci. Guilfoile, P.G., Hutchinson, C.R. J. Bacteriol. (1992) [Pubmed]
  18. Characterisation of actI-homologous DNA encoding polyketide synthase genes from the monensin producer Streptomyces cinnamonensis. Arrowsmith, T.J., Malpartida, F., Sherman, D.H., Birch, A., Hopwood, D.A., Robinson, J.A. Mol. Gen. Genet. (1992) [Pubmed]
  19. Analysis of the nucleotide sequence of the Streptomyces glaucescens tcmI genes provides key information about the enzymology of polyketide antibiotic biosynthesis. Bibb, M.J., Biró, S., Motamedi, H., Collins, J.F., Hutchinson, C.R. EMBO J. (1989) [Pubmed]
  20. Crystallization and preliminary X-ray analysis of tetracenomycin A2 oxygenase: a flavoprotein hydroxylase involved in polyketide biosynthesis. Beynon, J., Rafanan, E.R., Shen, B., Fisher, A.J. Acta Crystallogr. D Biol. Crystallogr. (2000) [Pubmed]
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