Specificity and promiscuity at the branch point in gentamicin biosynthesis

Chemistry and Biology

Volumn 21, Issue 5, 2014, Pages 608-618

  Guo, Junhong ^a   Huang, Fanglu ^b   Huang, Chuan ^a   Duan, Xiaobo ^a   Jian, Xinyun ^a   Leeper, Finian ^b   Deng, Zixin ^a   Leadlay, Peter F ^b   Sun, Yuhui ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINOTRANSFERASE; ENZYME GENB1; ENZYME GENB2; ENZYME GENB3; ENZYME GENB4; ENZYME GENK; ENZYME GENQ; GENTAMICIN; GENTAMICIN C COMPLEX; KETONE; OXIDOREDUCTASE; PYRIDOXAL 5 PHOSPHATE; UNCLASSIFIED DRUG; METHYLTRANSFERASE;

ARTICLE; BIOSYNTHESIS; CATALYSIS; DEHYDROGENATION; DRUG STRUCTURE; EPIMERIZATION; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHYLATION; MICROMONOSPORA; MICROMONOSPORA ECHINOSPORA; NONHUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN EXPRESSION; TRANSAMINATION; BIOCATALYSIS; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; ENZYME SPECIFICITY; METABOLISM; MOLECULAR GENETICS;

BACTERIA (MICROORGANISMS); NEGIBACTERIA;

BIOCATALYSIS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; GENTAMICINS; METHYLTRANSFERASES; MOLECULAR SEQUENCE DATA; SUBSTRATE SPECIFICITY;

EID: 84901457548     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2014.03.005     Document Type: Article

References (49)

1. K.M.A. Aboshanab Genetic studies on the biosynthesis of the major aminoglycoside antibiotics: isolation, analysis and comparison of the biosynthetic gene clusters for 12 aminoglycoside antibiotics. PhD thesis 2005 Bergische Universität Wuppertal, Germany
2. J. Bérdy, J.K. Pauncz, Z.M. Vajna, G. Horváth, J. Gyimesi, and I. Koczka Metabolites of gentamicin-producing Micromonospora species I. Isolation and identification of metabolites J. Antibiot. 30 1977 945 954
3. D. Bockenhauer, M.J. Hug, and R. Kleta Cystic fibrosis, aminoglycoside treatment and acute renal failure: the not so gentle micin Pediatr. Nephrol. 24 2009 925 928
4. D. Clausnitzer, W. Piepersberg, and U.F. Wehmeier The oxidoreductases LivQ and NeoQ are responsible for the different 6′-modifications in the aminoglycosides lividomycin and neomycin J. Appl. Microbiol. 111 2011 642 651
5. M.F. Cuccarese, A. Singh, M. Amiji, and G.A. O'Doherty A novel use of gentamicin in the ROS-mediated sensitization of NCI-H460 lung cancer cells to various anticancer agents ACS Chem. Biol. 8 2013 2771 2777
6. F. Del Vecchio, H. Petkovic, S.G. Kendrew, L. Low, B. Wilkinson, R. Lill, J. Cortés, B.A.M. Rudd, J. Staunton, and P.F. Leadlay Active-site residue, domain and module swaps in modular polyketide synthases J. Ind. Microbiol. Biotechnol. 30 2003 489 494 (Pubitemid 37214969)
7. Q.Z. Fan, F.L. Huang, P.F. Leadlay, and J.B. Spencer The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: genetic and biochemical evidence for the roles of two glycosyltransferases and a deacetylase Org. Biomol. Chem. 6 2008 3306 3314
8. M. Hainrichson, I. Nudelman, and T. Baasov Designer aminoglycosides: the race to develop improved antibiotics and compounds for the treatment of human genetic diseases Org. Biomol. Chem. 6 2008 227 239
9. W.R. Hong, and L.B. Yan Identification of gntK, a gene required for the methylation of purpurosamine C-6′ in gentamicin biosynthesis J. Gen. Appl. Microbiol. 58 2012 349 356
10. W.R. Hong, M. Ge, Z.H. Zeng, L. Zhu, M.Y. Luo, L. Shao, and D.J. Chen Molecular cloning and sequence analysis of the sisomicin biosynthetic gene cluster from Micromonospora inyoensis Biotechnol. Lett. 31 2009 449 455
11. J.L. Houghton, K.D. Green, W. Chen, and S. Garneau-Tsodikova The future of aminoglycosides: the end or renaissance? ChemBioChem 11 2010 880 902
12. F.L. Huang, S.F. Haydock, T. Mironenko, D. Spiteller, Y. Li, and J.B. Spencer The neomycin biosynthetic gene cluster of Streptomyces fradiae NCIMB 8233: characterisation of an aminotransferase involved in the formation of 2-deoxystreptamine Org. Biomol. Chem. 3 2005 1410 1418
13. F.L. Huang, D. Spiteller, N.A. Koorbanally, Y. Li, N.M. Llewellyn, and J.B. Spencer Elaboration of neosamine rings in the biosynthesis of neomycin and butirosin ChemBioChem 8 2007 283 288 (Pubitemid 47194508)
14. S. Karki, J.Y. Kim, S.H. Park, and H.J. Kwon Gene inactivation study on gntK, a putative C-methyltransferase gene in gentamicin biosynthesis from Micromonospora echinospora J. Kor. Soc. Appl. Biol. Chem. 55 2012 439 442
15. H. Kase, Y. Odakura, and K. Nakayama Sagamicin and the related aminoglycosides: fermentation and biosynthesis. I. Biosynthetic studies with the blocked mutants of Micromonospora sagamiensis J. Antibiot. 35 1982 1 9 (Pubitemid 12069733)
16. H. Kase, G. Shimura, T. Iida, and K. Nakayama Biotransformation of sisomicin and verdamicin by Micromonospora sagamiensis Agric. Biol. Chem. 46 1982 515 522 (Pubitemid 12087955)
17. M.K. Kharel, D.B. Basnet, H.C. Lee, K. Liou, J.S. Woo, B.G. Kim, and J.K. Sohng Isolation and characterization of the tobramycin biosynthetic gene cluster from Streptomyces tenebrarius FEMS Microbiol. Lett. 230 2004 185 190 (Pubitemid 38130199)
18. M.K. Kharel, D.B. Basnet, H.C. Lee, K. Liou, Y.H. Moon, J.J. Kim, J.S. Woo, and J.K. Sohng Molecular cloning and characterization of a 2-deoxystreptamine biosynthetic gene cluster in gentamicin-producing Micromonospora echinospora ATCC15835 Mol. Cells 18 2004 71 78 (Pubitemid 39386657)
19. M.K. Kharel, B. Subba, D.B. Basnet, J.S. Woo, H.C. Lee, K. Liou, and J.K. Sohng A gene cluster for biosynthesis of kanamycin from Streptomyces kanamyceticus: comparison with gentamicin biosynthetic gene cluster Arch. Biochem. Biophys. 429 2004 204 214 (Pubitemid 39093829)
20. J.Y. Kim, J.W. Suh, S.H. Kang, T.H. Phan, S.H. Park, and H.J. Kwon Gene inactivation study of gntE reveals its role in the first step of pseudotrisaccharide modifications in gentamicin biosynthesis Biochem. Biophys. Res. Commun. 372 2008 730 734
21. H.J. Kim, R.M. McCarty, Y. Ogasawara, Y.N. Liu, S.O. Mansoorabadi, J. LeVieux, and H.W. Liu GenK-catalyzed C-6′ methylation in the biosynthesis of gentamicin: isolation and characterization of a cobalamin-dependent radical SAM enzyme J. Am. Chem. Soc. 135 2013 8093 8096
22. M. Kobayashi, M. Sone, M. Umemura, T. Nabeshima, T. Nakashima, and S. Hellström Comparisons of cochleotoxicity among three gentamicin compounds following intratympanic application Acta Otolaryngol. 128 2008 245 249 (Pubitemid 351264433)
23. F. Kudo, and T. Eguchi Biosynthetic genes for aminoglycoside antibiotics J. Antibiot. 62 2009 471 481
24. F. Kudo, H. Sucipto, and T. Eguchi Enzymatic activity of a glycosyltransferase KanM2 encoded in the kanamycin biosynthetic gene cluster J. Antibiot. 62 2009 707 710
25. B.K. Lee, J.V. Bailey, R.G. Condon, J.A. Marquez, G.H. Wagman, and M.J. Weinstein Biotransformation of sisomicin to gentamicin C2b Antimicrob. Agents Chemother. 12 1977 335 338
26. D. Li, H. Li, X. Ni, H. Zhang, and H.Z. Xia Construction of a gentamicin C1a-overproducing strain of Micromonospora purpurea by inactivation of the gacD gene Microbiol. Res. 168 2013 263 267
27. L. Linde, and B. Kerem Introducing sense into nonsense in treatments of human genetic diseases Trends Genet. 24 2008 552 563
28. N.M. Llewellyn, and J.B. Spencer Biosynthesis of 2-deoxystreptamine- containing aminoglycoside antibiotics Nat. Prod. Rep. 23 2006 864 874 (Pubitemid 44808990)
29. D.J. MacNeil, J.L. Occi, K.M. Gewain, T. MacNeil, P.H. Gibbons, C.L. Ruby, and S.J. Danis Complex organization of the Streptomyces avermitilis genes encoding the avermectin polyketide synthase Gene 115 1992 119 125
30. D. Missiakas, C. Georgopoulos, and S. Raina The Escherichia coli heat shock gene htpY: mutational analysis, cloning, sequencing, and transcriptional regulation J. Bacteriol. 175 1993 2613 2624 (Pubitemid 23124901)
31. Y. Ota, H. Tamegai, F. Kudo, H. Kuriki, A. Koike-Takeshita, T. Eguchi, and K. Kakinuma Butirosin-biosynthetic gene cluster from Bacillus circulans J. Antibiot. 53 2000 1158 1167
32. J.W. Park, J.S. Hong, N. Parajuli, W.S. Jung, S.R. Park, S.K. Lim, J.K. Sohng, and Y.J. Yoon Genetic dissection of the biosynthetic route to gentamicin A2 by heterologous expression of its minimal gene set Proc. Natl. Acad. Sci. USA 105 2008 8399 8404 (Pubitemid 351904767)
33. J.W. Park, S.R. Park, K.K. Nepal, A.R. Han, Y.H. Ban, Y.J. Yoo, E.J. Kim, E.M. Kim, D. Kim, J.K. Sohng, and Y.J. Yoon Discovery of parallel pathways of kanamycin biosynthesis allows antibiotic manipulation Nat. Chem. Biol. 7 2011 843 852
34. S.R. Park, J.W. Park, Y.H. Ban, J.K. Sohng, and Y.J. Yoon 2-Deoxystreptamine-containing aminoglycoside antibiotics: recent advances in the characterization and manipulation of their biosynthetic pathways Nat. Prod. Rep. 30 2013 11 20
35. H. Reimann, D.J. Cooper, A.K. Mallams, R.S. Jaret, A. Yehaskel, M. Kugelman, H.F. Vernay, and D. Schumacher The structure of sisomicin, a novel unsaturated aminocyclitol antibiotic from Micromonospora inyoensis J. Org. Chem. 39 1974 1451 1457
36. R.M. Sandoval, J.P. Reilly, W. Running, S.B. Campos, J.R. Santos, C.L. Phillips, and B.A. Molitoris A non-nephrotoxic gentamicin congener that retains antimicrobial efficacy J. Am. Soc. Nephrol. 17 2006 2697 2705 (Pubitemid 44484660)
37. L. Shao, J.S. Chen, C.X. Wang, J.A. Li, Y.M. Tang, D.J. Chen, and W. Liu Characterization of a key aminoglycoside phosphotransferase in gentamicin biosynthesis Bioorg. Med. Chem. Lett. 23 2013 1438 1441
38. B. Subba, M.K. Kharel, H.C. Lee, K. Liou, B.G. Kim, and J.K. Sohng The ribostamycin biosynthetic gene cluster in Streptomyces ribosidificus: comparison with butirosin biosynthesis Mol. Cells 20 2005 90 96
39. Y.H. Sun, X.Y. He, J.D. Liang, X.F. Zhou, and Z.X. Deng Analysis of functions in plasmid pHZ1358 influencing its genetic and structural stability in Streptomyces lividans 1326 Appl. Microbiol. Biotechnol. 82 2009 303 310
40. R.T. Testa, and B.C. Tilley Biotransformation, a new approach to aminoglycoside biosynthesis. I. Sisomicin J. Antibiot. 28 1975 573 579
41. R.T. Testa, and B.C. Tilley Biotransformation, a new approach to aminoglycoside biosynthesis: II. Gentamicin J. Antibiot. 29 1976 140 146
42. C.J. Thibodeaux, C.E. Melançon 3rd, and H.W. Liu Natural-product sugar biosynthesis and enzymatic glycodiversification Angew. Chem. Int. Ed. Engl. 47 2008 9814 9859
43. J. Unwin, S. Standage, D. Alexander, T. Hosted Jr., A.C. Horan, and E.M. Wellington Gene cluster in Micromonospora echinospora ATCC15835 for the biosynthesis of the gentamicin C complex J. Antibiot. 57 2004 436 445 (Pubitemid 39162300)
44. S.A. Waksman, and H.A. Lechevalier Neomycin, a new antibiotic active against Streptomycin-resistant bacteria, including tuberculosis organisms Science 109 1949 305 307
45. M.J. Weinstein, G.M. Luedemann, E.M. Oden, and G.H. Wagman Gentamicin, a new broad-spectrum antibiotic complex Antimicrob Agents Chemother (Bethesda) 161 1963 1 7
46. M.J. Weinstein, G.H. Wagman, J.A. Marquez, R.T. Testa, and J.A. Waitz Verdamicin, a new broad spectrum aminoglycoside antibiotic Antimicrob. Agents Chemother. 7 1975 246 249
47. C.J. Wilkinson, Z.A. Hughes-Thomas, C.J. Martin, I. Böhm, T. Mironenko, M. Deacon, M. Wheatcroft, G. Wirtz, J. Staunton, and P.F. Leadlay Increasing the efficiency of heterologous promoters in actinomycetes J. Mol. Microbiol. Biotechnol. 4 2002 417 426 (Pubitemid 34784704)
48. K. Yokoyama, Y. Yamamoto, F. Kudo, and T. Eguchi Involvement of two distinct N-acetylglucosaminyltransferases and a dual-function deacetylase in neomycin biosynthesis ChemBioChem 9 2008 865 869
49. Q. Zhang, W.A. van der Donk, and W. Liu Radical-mediated enzymatic methylation: a tale of two SAMS Acc. Chem. Res. 45 2012 555 564