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Chemical Compound Review

Aklavinon     methyl (1R,2R,4S)-2-ethyl-2,4,5,7...

Synonyms: Aclavinone, Aklavinone, SureCN116665, CCRIS 7635, AG-K-24359, ...
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Disease relevance of Aklavinone


High impact information on Aklavinone


Chemical compound and disease context of Aklavinone


Biological context of Aklavinone

  • The phenotype of a dnrF mutant generated by gene disruption supports the idea that the dnrF gene encodes aklavinone 11-hydroxylase [9].
  • Strain H039 accumulated aklavinone and H026, H035, H038 and H054 had mutations that changed glycosylation of aklavinone [10].
  • Respective products deduced from ORF1, ORF2, ORF3, and ORF5 were similar to the penicillin-binding protein 4 of Streptomyces lactamduras, the repressor protein AcrR of the acrAB operon, the enzyme RdmC involved in the biosynthesis of the antibiotic aklavinone, and IS801 transposase-like protein from Pseudomonas pseudoalcakigenes, respectively [11].

Associations of Aklavinone with other chemical compounds


Gene context of Aklavinone

  • When S. galilaeus ATCC 31671 was transformed with a plasmid carrying only the intact actIII gene (pANT45), aklavinone was formed exclusively [13].

Analytical, diagnostic and therapeutic context of Aklavinone


  1. Crystal structure of aclacinomycin methylesterase with bound product analogues: implications for anthracycline recognition and mechanism. Jansson, A., Niemi, J., Mäntsälä, P., Schneider, G. J. Biol. Chem. (2003) [Pubmed]
  2. Expression of Streptomyces peucetius genes for doxorubicin resistance and aklavinone 11-hydroxylase in Streptomyces galilaeus ATCC 31133 and production of a hybrid aclacinomycin. Hwang, C.K., Kim, H.S., Hong, Y.S., Kim, Y.H., Hong, S.K., Kim, S.J., Lee, J.J. Antimicrob. Agents Chemother. (1995) [Pubmed]
  3. Cloning, sequencing, and analysis of aklaviketone reductase from Streptomyces sp. strain C5. Dickens, M.L., Ye, J., Strohl, W.R. J. Bacteriol. (1996) [Pubmed]
  4. Nucleotide sequence of the aknA region of the aklavinone biosynthetic gene cluster of Streptomyces galilaeus. Tsukamoto, N., Fujii, I., Ebizuka, Y., Sankawa, U. J. Bacteriol. (1994) [Pubmed]
  5. Streptomyces peucetius daunorubicin biosynthesis gene, dnrF: sequence and heterologous expression. Filippini, S., Solinas, M.M., Breme, U., Schlüter, M.B., Gabellini, D., Biamonti, G., Colombo, A.L., Garofano, L. Microbiology (Reading, Engl.) (1995) [Pubmed]
  6. Modification of aklavinone and aclacinomycins in vitro and in vivo by rhodomycin biosynthesis gene products. Wang, Y., Niemi, J., Mäntsälä, P. FEMS Microbiol. Lett. (2002) [Pubmed]
  7. New anthracycline metabolites from mutant strains of Streptomyces galilaeus MA144-M1. II. Structure of 2-hydroxyaklavinone and new aklavinone glycosides. Matsuzawa, Y., Yoshimoto, A., Shibamoto, N., Tobe, H., Oki, T., Naganawa, H., Takeuchi, T., Umezawa, H. J. Antibiot. (1981) [Pubmed]
  8. New betaclamycin and aclarubicin analogs obtained by prolonged microbial conversion with an aclarubicin-negative mutant. Johdo, O., Yoshioka, T., Naganawa, H., Takeuchi, T., Yoshimoto, A. J. Antibiot. (1996) [Pubmed]
  9. Molecular cloning and characterization of the aklavinone 11-hydroxylase gene of Streptomyces peucetius subsp. caesius ATCC 27952. Hong, Y.S., Hwang, C.K., Hong, S.K., Kim, Y.H., Lee, J.J. J. Bacteriol. (1994) [Pubmed]
  10. Isolation and characterization of aclacinomycin A-non-producing Streptomyces galilaeus (ATCC 31615) mutants. Ylihonko, K., Hakala, J., Niemi, J., Lundell, J., Mäntsälä, P. Microbiology (Reading, Engl.) (1994) [Pubmed]
  11. Nucleotide sequence of the gene cluster containing the mphB gene for macrolide 2'-phosphotransferase II. Katayama, J., Noguchi, N. Biol. Pharm. Bull. (1999) [Pubmed]
  12. Cloning and characterization of Streptomyces galilaeus aclacinomycins polyketide synthase (PKS) cluster. Räty, K., Kantola, J., Hautala, A., Hakala, J., Ylihonko, K., Mäntsälä, P. Gene (2002) [Pubmed]
  13. Biosynthesis of anthraquinones by interspecies cloning of actinorhodin biosynthesis genes in streptomycetes: clarification of actinorhodin gene functions. Bartel, P.L., Zhu, C.B., Lampel, J.S., Dosch, D.C., Connors, N.C., Strohl, W.R., Beale, J.M., Floss, H.G. J. Bacteriol. (1990) [Pubmed]
  14. Characterization of polyketide ketoreductase gene (MPKR) from midecamycin-producing strain (Streptomyces mycarofaciens 1748). Xia, H., Wang, Y., Sun, J. Chin. J. Biotechnol. (1994) [Pubmed]
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