Two genes, rif15 and rif16, of the rifamycin biosynthetic gene cluster in Amycolatopsis mediterranei likely encode a transketolase and a P450 monooxygenase, respectively, both essential for the conversion of rifamycin SV into B

Acta Biochimica et Biophysica Sinica

Volumn 43, Issue 12, 2011, Pages 948-956

  Yuan, Hua ^a   Zhao, Wei ^a,b   Zhong, Yi ^a   Wang, Jin ^c   Qin, Zhongjun ^a   Ding, Xiaoming ^b   Zhao, Guo Ping ^a,b,c,d  

^a INSTITUTE OF PLANT PHYSIOLOGY AND ECOLOGY   (China)

^b FUDAN UNIVERSITY   (China)

^c CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^d CHINESE NATIONAL HUMAN GENOME CENTER AT SHANGHAI   (China)

Author keywords

Amycolatopsis mediterranei; P450; Rifamycin; Transketolase

Indexed keywords

ANTIINFECTIVE AGENT; MIXED FUNCTION OXIDASE; RIFAMYCIN; RIFAMYCIN B; TRANSKETOLASE;

ACTINOMYCETACEAE; ARTICLE; BIOSYNTHESIS; GENETICS; METABOLISM; MULTIGENE FAMILY;

ACTINOMYCETACEAE; ANTI-BACTERIAL AGENTS; MIXED FUNCTION OXYGENASES; MULTIGENE FAMILY; RIFAMYCINS; TRANSKETOLASE;

EID: 82255164179     PISSN: 16729145     EISSN: 17457270     Source Type: Journal    
DOI: 10.1093/abbs/gmr091     Document Type: Article

References (24)

1. Floss HG and Yu TW. Rifamycin-mode of action, resistance, and biosynthesis. Chem Rev 2005, 105: 621-632.
2. Dye C, Williams BG, Espinal MA and Raviglione MC. Erasing the world's slow stain: strategies to beat multidrug-resistant tuberculosis. Science 2002, 295: 2042-2046. (Pubitemid 34229458)
3. Admiraal SJ, Walsh CT and Khosla C. The loading module of rifamycin synthetase is an adenylation-thiolation didomain with substrate tolerance for substituted benzoates. Biochemistry 2001, 40: 6116-6123. (Pubitemid 32466316)
4. Admiraal SJ, Khosla C and Walsh CT. The loading and initial elongation modules of rifamycin synthetase collaborate to produce mixed aryl ketide products. Biochemistry 2002, 41: 5313-5324. (Pubitemid 34411688)
5. Xu J, Wan E, Kim CJ, Floss HG and Mahmud T. Identification of tailoring genes involved in the modification of the polyketide backbone of rifamycin B by Amycolatopsis mediterranei S699. Microbiology 2005, 151: 2515-2528. (Pubitemid 41149775)
6. White RJ, Martinelli E, Gallo GG, Lancini G and Beynon P. Rifamycin biosynthesis studied with 13C enriched precursors and carbon magnetic resonance. Nature 1973, 243: 273-277.
7. August PR, Tang L, Yoon YJ, Ning S, Muller R, Yu TW and Taylor M, et al. Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699. Chem Biol 1998, 5: 69-79. (Pubitemid 28199136)
8. Ghisalba O, Roos R, Schupp T and Nuesch J. Transformation of rifamycin S into rifamycins B and L. A revision of the current biosynthetic hypothesis. J Antibiot (Tokyo) 1982, 35: 74-80. (Pubitemid 12069742)
9. Guo J and Frost JW. Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom. J Am Chem Soc 2002, 124: 10642-10643.
10. Xiong Y, Wu X and Mahmud T. A homologue of the Mycobacterium tuberculosis PapA5 protein, Rif-Orf20, is an acetyltransferase involved in the biosynthesis of antitubercular drug rifamycin B by Amycolatopsis mediterranei S699. Chembiochem 2005, 6: 834-837. (Pubitemid 40873743)
11. Xu J, Mahmud T and Floss HG. Isolation and characterization of 27-O-demethylrifamycin SV methyltransferase provides new insights into the post-PKS modification steps during the biosynthesis of the antitubercular drug rifamycin B by Amycolatopsis mediterranei S699. Arch Biochem Biophys 2003, 411: 277-288. (Pubitemid 36298656)
12. Zhao W, Zhong Y, Yuan H, Wang J, Zheng H, Wang Y and Cen X, et al. Complete genome sequence of the rifamycin SV-producing Amycolatopsis mediterranei U32 revealed its genetic characteristics in phylogeny and metabolism. Cell Res 2010, 20: 1096-1108.
13. Penn K, Jenkins C, Nett M, Udwary DW, Gontang EA, McGlinchey RP and Foster B, et al. Genomic islands link secondary metabolism to functional adaptation in marine Actinobacteria. ISME J 2009, 3: 1193-1203.
14. Wilson MC, Gulder TA, Mahmud T and Moore BS. Shared biosynthesis of the saliniketals and rifamycins in Salinispora arenicola is controlled by the sare1259-encoded cytochrome P450. J Am Chem Soc 2010, 132: 12757-12765.
15. Kieser T, Bibb MJ, Buttner MJ, Chater KF and Hopwood DA. Practical Streptomyces Genetics. UK: The John Innes Foundation Press, 2000.
16. Yu H, Peng WT, Liu Y, Wu T, Yao YF, Cui MX and Jiang WH, et al. Identification and characterization of glnA promoter and its corresponding trans-regulatory protein GlnR in the rifamycin SV producing actinomycete, Amycolatopsis mediterranei U32. Acta Biochim Biophys Sin 2006, 38: 831-843. (Pubitemid 44952886)
17. Ding X, Tian Y, Chiao J, Zhao G and Jiang W. Stability of plasmid pA387 derivatives in Amycolatopsis mediterranei producing rifamycin. Biotechnol Lett 2003, 25: 1647-1652. (Pubitemid 37189970)
18. Sambandamurthy VK, Wang X, Chen B, Russell RG, Derrick S, Collins FM and Morris SL, et al. A pantothenate auxotroph of Mycobacterium tuberculosis is highly attenuated and protects mice against tuberculosis. Nat Med 2002, 8: 1171-1174. (Pubitemid 35175974)
19. Beggs ML, Crawford JT and Eisenach KD. Isolation and sequencing of the replication region of Mycobacterium avium plasmid pLR7. J Bacteriol 1995, 177: 4836-4840.
20. Munro AW, Girvan HM and McLean KJ. Variations on a (t)heme-novel mechanisms, redox partners and catalytic functions in the cytochrome P450 superfamily. Nat Prod Rep 2007, 24: 585-609. (Pubitemid 46848711)
21. Xu LH, Fushinobu S, Takamatsu S, Wakagi T, Ikeda H and Shoun H. Regio- and stereospecificity of filipin hydroxylation sites revealed by crystal structures of cytochrome P450 105P1 and 105D6 from Streptomyces avermitilis. J Biol Chem 2010, 285: 16844-16853.
22. Guo J and Frost JW. Biosynthesis of 1-deoxy-1-imino-D-erythrose 4- phosphate: a defining metabolite in the aminoshikimate pathway. J Am Chem Soc 2002, 124: 528-529. (Pubitemid 34101155)
23. Yu TW, Muller R, Muller M, Zhang X, Draeger G, Kim CG and Leistner E, et al. Mutational analysis and reconstituted expression of the biosynthetic genes involved in the formation of 3-amino-5-hydroxybenzoic acid, the starter unit of rifamycin biosynthesis in Amycolatopsis mediterranei S699. J Biol Chem 2001, 276: 12546-12555.
24. Fiedler E, Golbik R, Schneider G, Tittmann K, Neef H, Konig S and Hubner G. Examination of donor substrate conversion in yeast transketolase. J Biol Chem 2001, 276: 16051-16058.