Post-PKS tailoring steps of the spiramycin macrolactone ring in streptomyces ambofaciens

Antimicrobial Agents and Chemotherapy

Volumn 57, Issue 8, 2013, Pages 3836-3842

  Nguyen, Hoang Chuong ^a,b,c   Darbon, Emmanuelle ^a,b   Thai, Robert ^d   Pernodet, Jean Luc ^a,b   Lautru, Sylvie ^a,b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNRS   (France)

^c UNIVERSITY OF NATURAL SCIENCES   (Viet Nam)

^d SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; CYTOCHROME P450; FORMALDEHYDE; MACROLIDE; METHYL GROUP; POLYKETIDE SYNTHASE; SPIRAMYCIN;

ACYLATION; ANTIBACTERIAL ACTIVITY; ARTICLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL REACTION; ENZYME INACTIVATION; GENE CLUSTER; GLYCOSYLATION; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REDUCTION; STREPTOMYCES AMBOFACIENS;

ACYLATION; ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; FORMALDEHYDE; GENE SILENCING; GENES, BACTERIAL; GLUCOSAMINE; GLYCOSYLATION; HEXOSAMINES; MACROLIDES; OXIDATION-REDUCTION; POLYKETIDE SYNTHASES; SEQUENCE DELETION; SPECIES SPECIFICITY; SPIRAMYCIN; STREPTOMYCES; TIME FACTORS;

EID: 84880306298     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00512-13     Document Type: Article

References (30)

1. Chew WK, Segarra I, Ambu S, Mak JW. 2012. Significant reduction of brain cysts caused by Toxoplasma gondii after treatment with spiramycin coadministered with metronidazole in a mouse model of chronic toxoplasmosis. Antimicrob. Agents Chemother. 56:1762-1768.
2. Valentini P, Annunziata ML, Angelone DF, Masini L, De Santis M, Testa A, Grillo RL, Speziale D, Ranno O. 2009. Role of spiramycin/ cotrimoxazole association in the mother-to-child transmission of toxoplasmosis infection in pregnancy. Eur. J. Clin. Microbiol. Infect. Dis. 28: 297-300.
3. Poulet P-P, Duffaut D, Barthet P, Brumpt I. 2005. Concentrations and in vivo antibacterial activity of spiramycin and metronidazole in patients with periodontitis treated with high-dose metronidazole and the spiramycin/ metronidazole combination. J. Antimicrob. Chemother. 55:347-351.
4. Dumitrescu AL (ed). 2011. Antibiotics and antiseptics in periodontal therapy. Springer, Berlin, Germany.
5. Richardson MA, Kuhstoss S, Huber ML, Ford L, Godfrey O, Turner JR, Rao RN. 1990. Cloning of spiramycin biosynthetic genes and their use in constructing Streptomyces ambofaciens mutants defective in spiramycin biosynthesis. J. Bacteriol. 172:3790-3798.
6. Geistlich M, Losick R, Turner JR, Rao RN. 1992. Characterization of a novel regulatory gene governing the expression of a polyketide synthase gene in Streptomyces ambofaciens. Mol. Microbiol. 6:2019-2029.
7. Kuhstoss S, Huber M, Turner JR, Paschal JW, Rao RN. 1996. Production of a novel polyketide through the construction of a hybrid polyketide synthase. Gene 183:231-236.
8. Karray F, Darbon E, Oestreicher N, Dominguez H, Tuphile K, Gagnat J, Blondelet-Rouault MH, Gerbaud C, Pernodet J-L. 2007. Organization of the biosynthetic gene cluster for the macrolide antibiotic spiramycin in Streptomyces ambofaciens. Microbiology (Reading, Engl.) 153:4111-4122.
9. Omura S (ed). 1984. Macrolide antibiotics: chemistry, biology, and practice. Academic Press, Orlando, FL.
10. Nguyen HC, Karray F, Lautru S, Gagnat J, Lebrihi A, Huynh TDH, Pernodet J-L. 2010. Glycosylation steps during spiramycin biosynthesis in Streptomyces ambofaciens: involvement of three glycosyltransferases and their interplay with two auxiliary proteins. Antimicrob. Agents Chemother. 54:2830-2839.
11. Sambrook J, Russell DW. 2001. Molecular cloning: a laboratory manual, 3rd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
12. Kieser T, Bibb MJ, Buttner MJ, Chater KK, Hopwood DA. 2000. Practical Streptomyces genetics. John Innes Foundation, Norwich, United Kingdom.
13. Pernodet JL, Alegre MT, Blondelet-Rouault MH, Guérineau M. 1993. Resistance to spiramycin in Streptomyces ambofaciens, the producer organism, involves at least two different mechanisms. J. Gen. Microbiol. 139:1003-1011.
14. Gust B, Chandra G, Jakimowicz D, Yuqing T, Bruton CJ, Chater KF. 2004. Lambda red-mediated genetic manipulation of antibioticproducing Streptomyces. Adv. Appl. Microbiol. 54:107-128.
15. Chaveroche MK, Ghigo JM, D'Enfert C. 2000. A rapid method for efficient gene replacement in the filamentous fungus Aspergillus nidulans. Nucleic Acids Res. 28:e97. doi:10.1093/nar/28.22.e97.
16. Gourmelen A, Blondelet-Rouault MH, Pernodet JL. 1998. Characterization of a glycosyl transferase inactivating macrolides, encoded by gimA from Streptomyces ambofaciens. Antimicrob. Agents Chemother. 42:2612-2619.
17. Merson-Davies LA, Cundliffe E. 1994. Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome. Mol. Microbiol. 13:349-355.
18. Iizaka Y, Higashi N, Ishida M, Oiwa R, Ichikawa Y, Takeda M, Anzai Y, Kato F. 2013. Function of cytochrome P450 enzymes RosC and RosD in the biosynthesis of rosamicin macrolide antibiotic produced by Micromonospora rosaria. Antimicrob. Agents Chemother. 57:1529-1531.
19. Pendela M, Govaerts C, Diana J, Hoogmartens J, Van Schepdael A, Adams E. 2007. Characterization of impurities in spiramycin by liquid chromatography/ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 21:599-613.
20. Van Poucke C, De Keyser K, Baltusnikiene A, McEvoy JD, Van Peteghem C. 2003. Liquid chromatographic-tandem mass spectrometric detection of banned antibacterial growth promoters in animal feed. Anal. Chim. Acta 483:99-109.
21. Omura S, Kitao C, Hamada H, Ikeda H,. 1979. Bioconversion and biosynthesis of 16-membered macrolide antibiotics. X. Final steps in the biosynthesis of spiramycin, using enzyme inhibitor: cerulenin. Chem. Pharm. Bull. (Tokyo) 27:176-182.
22. Ikeda H, Nonomiya T, Usami M, Ohta T, Omura S. 1999. Organization of the biosynthetic gene cluster for the polyketide anthelmintic macrolide avermectin in Streptomyces avermitilis. Proc. Natl. Acad. Sci. U. S. A. 96: 9509-9514.
23. Wang X-J, Wang C-Q, Sun X-L, Xiang W-S. 2010. 5-Ketoreductase from Streptomyces bingchengensis: overexpression and preliminary characterization. Biotechnol. Lett. 32:1497-1502.
24. Remsing LL, González AM, Nur-e-Alam M, Fernández-Lozano MJ, Braña AF, Rix U, Oliveira MA, Méndez C, Salas JA, Rohr J. 2003. Mithramycin SK, a novel antitumor drug with improved therapeutic index, mithramycin SA, and demycarosyl-mithramycin SK: three new products generated in the mithramycin producer Streptomyces argillaceus through combinatorial biosynthesis. J. Am. Chem. Soc. 125:5745-5753.
25. Marchler-Bauer A, Bryant SH. 2004. CD-Search: protein domain annotations on the fly. Nucleic Acids Res. 32:W327-W331.
26. Karray F, Darbon E, Nguyen HC, Gagnat J, Pernodet J-L. 2010. Regulation of the biosynthesis of the macrolide antibiotic spiramycin in Streptomyces ambofaciens. J. Bacteriol. 192:5813-5821.
27. Huang SL, Hassell TC, Yeh WK. 1993. Purification and properties of NADPH-dependent tylosin reductase from Streptomyces fradiae. J. Biol. Chem. 268:18987-18993.
28. Baltz RH, Seno ET, Stonesifer J, Wild GM. 1983. Biosynthesis of the macrolide antibiotic tylosin. A preferred pathway from tylactone to tylosin. J. Antibiot. 36:131-141.
29. Baltz RH, Seno ET. 1981. Properties of Streptomyces fradiae mutants blocked in biosynthesis of the macrolide antibiotic tylosin. Antimicrob. Agents Chemother. 20:214-225.
30. Omura S, Sadakane N, Tanaka Y, Matsubara H. 1983. Chimeramycins: new macrolide antibiotics produced by hybrid biosynthesis. J. Antibiot. 36:927-930.