Capturing linear intermediates and C-terminal variants during maturation of the thiopeptide GE2270

Chemistry and Biology

Volumn 20, Issue 8, 2013, Pages 1067-1077

  Tocchetti, Arianna ^a   Maffioli, Sonia ^b   Iorio, Marianna ^b   Alt, Silke ^b   Mazzei, Emma ^b   Brunati, Cristina ^b   Sosio, Margherita ^a,b   Donadio, Stefano ^a,b  

^a Ktedogen Srl   (Italy)

^b NAICONS Srl   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; MACROCYCLIC COMPOUND; OXAZOLINE DERIVATIVE; PEPTIDE DERIVATIVE; PYRIDINE; SERINE; THIOPEPTIDE GE 2270; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; GENE CLUSTER; GENE DELETION; HYDROXYLATION; METHYLATION; NONHUMAN; PRIORITY JOURNAL;

NONOMURAEA; PLANOBISPORA ROSEA; POSIBACTERIA;

EID: 84883150295     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2013.07.005     Document Type: Article

References (38)

1. M.G. Acker, A.A. Bowers, and C.T. Walsh Generation of thiocillin variants by prepeptide gene replacement and in vivo processing by Bacillus cereus J. Am. Chem. Soc. 131 2009 17563 17565
2. P.G. Arnison, M.J. Bibb, G. Bierbaum, A.A. Bowers, T.S. Bugni, G. Bulaj, J.A. Camarero, D.J. Campopiano, G.L. Challis, and J. Clardy Ribosomally synthesized and post-translationally modified peptide natural products: overview and recommendations for a universal nomenclature Nat. Prod. Rep. 30 2013 108 160
3. U.G. Bhat, M. Halasi, and A.L. Gartel FoxM1 is a general target for proteasome inhibitors PLoS ONE 4 2009 e6593
4. P.J. Belshaw, R.S. Roy, N.L. Kelleher, and C.T. Walsh Kinetics and regioselectivity of peptide-to-heterocycle conversions by microcin B17 synthetase Chem. Biol. 5 1998 373 384
5. T.M. Binz, S.I. Maffioli, M. Sosio, S. Donadio, and R. Müller Insights into an unusual nonribosomal peptide synthetase biosynthesis: identification and characterization of the GE81112 biosynthetic gene cluster J. Biol. Chem. 285 2010 32710 32719
6. A.A. Bowers, M.G. Acker, A. Koglin, and C.T. Walsh Manipulation of thiocillin variants by prepeptide gene replacement: structure, conformation, and activity of heterocycle substitution mutants J. Am. Chem. Soc. 132 2010 7519 7527
7. A.A. Bowers, M.G. Acker, T.S. Young, and C.T. Walsh Generation of thiocillin ring size variants by prepeptide gene replacement and in vivo processing by Bacillus cereus J. Am. Chem. Soc. 134 2012 10313 10316
8. M.S. Butler Natural products to drugs: natural product derived compounds in clinical trials Nat. Prod. Rep. 22 2005 162 195
9. L. Colombo, S. Stella, and E. Selva Contribution of mass spectrometry to the structural confirmation of components of the antibiotic GE2270 complex Rapid Commun. Mass Spectrom. 9 1995 717 722
10. K.A. Datsenko, and B.L. Wanner One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products Proc. Natl. Acad. Sci. USA 97 2000 6640 6645
11. M.T. De Pietro, A. Marazzi, M. Sosio, S. Donadio, and G. Lancini Biosynthesis of the thiazolylpeptide antibiotic GE2270 J. Antibiot. (Tokyo) 54 2001 1066 1071
12. S. Donadio, S. Maffioli, P. Monciardini, M. Sosio, and D. Jabes Antibiotic discovery in the twenty-first century: current trends and future perspectives J. Antibiot. (Tokyo) 63 2010 423 430
13. K.L. Dunbar, J.O. Melby, and D.A. Mitchell YcaO domains use ATP to activate amide backbones during peptide cyclodehydrations Nat. Chem. Biol. 8 2012 569 575
14. L.C. Foulston, and M.J. Bibb Microbisporicin gene cluster reveals unusual features of lantibiotic biosynthesis in actinomycetes Proc. Natl. Acad. Sci. USA 107 2010 13461 13466
15. L. Gastaldo, and F. Marinelli Changes in GE2270 antibiotic production in Planobispora rosea through modulation of methylation metabolism Microbiology 149 2003 1523 1532
16. J. Kettenring, L. Colombo, P. Ferrari, P. Tavecchia, M. Nebuloni, K. Vékey, G.G. Gallo, and E. Selva Antibiotic GE2270 a: a novel inhibitor of bacterial protein synthesis. II. Structure elucidation J. Antibiot. (Tokyo) 44 1991 702 715
17. T. Kieser, M.J. Bibb, M.J. Buttner, K.F. Chater, and D.A. Hopwood Practical Streptomyces Genetics 2000 Crowes Norwich, UK
18. M.J. LaMarche, J.A. Leeds, A. Amaral, J.T. Brewer, S.M. Bushell, G. Deng, J.M. Dewhurst, J. Ding, J. Dzink-Fox, and G. Gamber Discovery of LFF571: an investigational agent for Clostridium difficile infection J. Med. Chem. 55 2012 2376 2387
19. C. Li, F. Zhang, and W.L. Kelly Mutagenesis of the thiostrepton precursor peptide at Thr7 impacts both biosynthesis and function Chem. Commun. (Camb.) 48 2012 558 560
20. R. Liao, and W. Liu Thiostrepton maturation involving a deesterification-amidation way to process the C-terminally methylated peptide backbone J. Am. Chem. Soc. 133 2011 2852 2855
21. W. Liu, M. Ma, Y. Xue, N. Liu, S. Wang, and Y. Chen The C-terminal extended serine residue is absolutely required in nosiheptide maturation ChemBioChem 14 2013 573 576
22. S.J. Malcomson, T.S. Young, J.G. Ruby, P. Skewes-Cox, and C.T. Walsh The posttranslational modification cascade to the thiopeptide berninamycin generates linear forms and altered macrocyclic scaffolds Proc. Natl. Acad. Sci. USA 110 2013 8483 8488
23. R.P. Morris, J.A. Leeds, H.U. Naegeli, L. Oberer, K. Memmert, E. Weber, M.J. LaMarche, C.N. Parker, N. Burrer, and S. Esterow Ribosomally synthesized thiopeptide antibiotics targeting elongation factor Tu J. Am. Chem. Soc. 131 2009 5946 5955
24. A. Parmeggiani, I.M. Krab, S. Okamura, R.C. Nielsen, J. Nyborg, and P. Nissen Structural basis of the action of pulvomycin and GE2270 A on elongation factor Tu Biochemistry 45 2006 6846 6857
25. E.J. Sherwood, A.R. Hesketh, and M.J. Bibb Cloning and analysis of the planosporicin lantibiotic biosynthetic gene cluster of Planomonospora alba J. Bacteriol. 195 2013 2309 2321
26. E. Selva, G. Beretta, N. Montanini, G.S. Saddler, L. Gastaldo, P. Ferrari, R. Lorenzetti, P. Landini, F. Ripamonti, and B.P. Goldstein Antibiotic GE2270 a: a novel inhibitor of bacterial protein synthesis. I. Isolation and characterization J. Antibiot. (Tokyo) 44 1991 693 701
27. E. Selva, P. Ferrari, M. Kurz, P. Tavecchia, L. Colombo, S. Stella, E. Restelli, B.P. Goldstein, F. Ripamonti, and M. Denaro Components of the GE2270 complex produced by Planobispora rosea ATCC 53773 J. Antibiot. (Tokyo) 48 1995 1039 1042
28. M. Sosio, G. Amati, C. Cappellano, E. Sarubbi, F. Monti, and S. Donadio An elongation factor Tu (EF-Tu) resistant to the EF-Tu inhibitor GE2270 in the producing organism Planobispora rosea Mol. Microbiol. 22 1996 43 51
29. M. Sosio, S. Stinchi, F. Beltrametti, A. Lazzarini, and S. Donadio The gene cluster for the biosynthesis of the glycopeptide antibiotic A40926 by nonomuraea species Chem. Biol. 10 2003 541 549
30. S. Stinchi, S. Azimonti, S. Donadio, and M. Sosio A gene transfer system for the glycopeptide producer Nonomuraea sp. ATCC39727 FEMS Microbiol. Lett. 225 2003 53 57
31. P. Tavecchia, P. Gentili, M. Kurz, C. Sottani, R. Bonfichi, S. Lociuro, and E. Selva Revised structure of the antibiotic GE 2270A J. Antibiot. (Tokyo) 47 1994 1564 1567
32. C.T. Walsh, M.G. Acker, and A.A. Bowers Thiazolyl peptide antibiotic biosynthesis: a cascade of post-translational modifications on ribosomal nascent proteins J. Biol. Chem. 285 2010 27525 27531
33. J.M. Weber, J.O. Leung, S.J. Swanson, K.B. Idler, and J.B. McAlpine An erythromycin derivative produced by targeted gene disruption in Saccharopolyspora erythraea Science 252 1991 114 117
34. T.S. Young, and C.T. Walsh Identification of the thiazolyl peptide GE37468 gene cluster from Streptomyces ATCC 55365 and heterologous expression in Streptomyces lividans Proc. Natl. Acad. Sci. USA 108 2011 13053 13058
35. T.S. Young, P.C. Dorrestein, and C.T. Walsh Codon randomization for rapid exploration of chemical space in thiopeptide antibiotic variants Chem. Biol. 19 2012 1600 1610
36. Y. Yu, L. Duan, Q. Zhang, R. Liao, Y. Ding, H. Pan, E. Wendt-Pienkowski, G. Tang, B. Shen, and W. Liu Nosiheptide biosynthesis featuring a unique indole side ring formation on the characteristic thiopeptide framework ACS Chem. Biol. 4 2009 855 864
37. Y. Yu, H. Guo, Q. Zhang, L. Duan, Y. Ding, R. Liao, C. Lei, B. Shen, and W. Liu NosA catalyzing carboxyl-terminal amide formation in nosiheptide maturation via an enamine dealkylation on the serine-extended precursor peptide J. Am. Chem. Soc. 132 2010 16324 16326
38. Q. Zhang, and W. Liu Biosynthesis of thiopeptide antibiotics and their pathway engineering Nat. Prod. Rep. 30 2013 218 226