Kinetics and regioselectivity of peptide-to-heterocycle conversions by microcin B17 synthetase

Chemistry and Biology

Volumn 5, Issue 7, 1998, Pages 373-384

  Belshaw, Peter J ^a   Roy, Ranabir Sinha ^a   Kelleher, Neil L ^a   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Antibiotics; Microcin B17; Oxazole; Post translational modification; Thiazole

Indexed keywords

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 0032126996     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90071-0     Document Type: Article

References (19)

1. San Millan, J.L., Hernandez-Chico, C., Pereda, P. & Moreno, F. (1985). Cloning and mapping of the genetic determinants for microcin B17 production and immunity. J. Bacteriol. 163, 275-281.
2. Garrido, M.C., Herrero, M., Kolter, R. & Moreno, F. (1988). The export of the DNA replication inhibitor microcin B17 provides immunity for the host cell. EMBO J. 7, 1853-1862.
3. San Millan, J.L., Kolter, R. & Moreno, F. (1985). Plasmid genes required for microcin B17 production. J. Bacteriol. 163, 1016-1020.
4. Yorgey, P., et al., & Kolter, R. (1994). Posttranslational modifications in microcin B17 define an additonal class of DNA gyrase inhibitor. Proc. Natl Acad. Sci. USA 91, 4519-4523.
5. Bayer, A., Freund, S. & Jung, G. (1995). Post-translational heterocyclic backbone modifications in the 43-peptide antibiotic microcin B17. Structure elucidation and NMR study of a 13C, 15N-labelled gyrase inhibitor. Eur. J. Biochem. 234, 414-426.
6. Li, Y.M., Milne, J.C., Madison, L.L., Kolter, R. & Walsh, C.T. (1996). From peptide precursors to oxazole and thiazole-containing peptide antibiotics: microcin B17 synthase. Science 274, 1188-1193.
7. Yorgey, P., Davagnino, J. & Kolter, R. (1993). The maturation pathway of microcin B17, A peptide inhibitor of DNA gyrase. Mol. Microbiol. 9, 897-905.
8. Madison, L.L., Vivas, E.I., Li, Y.M., Walsh, C.T. & Kolter, R. (1997). The leader peptide is essential for the post-translational modification of the DNA-gyrase inhibitor microcin B17. Mol. Microbiol. 23, 161-168.
9. Sinha Roy, R., Belshaw, P.J. & Walsh, C.T. (1998). Mutational analysis of posttranslational heterocycle biosynthesis in the gyrase inhibitor microcin B17: distance dependence from propeptide and tolerance for substitution in a GSCG cyclizable sequence. Biochemistry 37, 4125-4136.
10. McLafferty, F.W. (1994). High-resolution tandem FT mass spectrometry above 10 kDa. Accounts Chem. Res. 27, 379-386.
11. Deng, W.P. & Nickoloff, J.A. (1992). Site-directed mutagenesis of virtually any plasmid by eliminating a unique site. Anal. Biochem. 200, 81-88.
12. Brookes, P., Clark, R.J., Fuller, A.T., Mijovic, M.P.V. & Walker, J. (1960). Chemistry of Micrococcin P. Part III. J. Chem. Soc. 916-925.
13. 1-26. Chem. Biol. 5, 217-228.
14. Kovacs, L., Herczegh, P., Batta, G. & Farkas, I. (1987). Two acyclic analogues of 2-β-D-ribofuranosyl thiazole-4-carboxamide (Tiazofuran). Heterocycles 26, 947-960.
15. Kane, S.A., Natrajan, A. & Hecht, S.M. (1994). On the role of the bithiazole moiety in sequence-selective DNA cleavage by Fe-bleomycin. J. Biol. Chem. 269, 10899-10904.
16. Vizan, J.L., Hernandez-Chico, C., del Castillo, I. & Moreno, F. (1991). The peptide antibiotic microcin B17 induces double-strand cleavage of DNA mediated by E. coli DNA gyrase. EMBO J. 10, 467-476.
17. Wilm, M. & Mann. M. (1996). Analytical properties of the nanoelectrospray ion source. Anal. Chem. 68, 1-8.
18. Cassady, C.J., Wronka, J., Kruppa, G.H. & Laukien, F.H. (1994). Deprotonation of multiply protonated ubiquitin ions. Rapid Commun. Mass Spectrom. 8, 394-400.
19. Kofel, P., Allemann, M., Kellerhals, H.P. & Wanczek, K.P. (1989). External trapped ion-source for ion cyclotron resonance spectrometry. Int. J. Mass Spectrom. Ion Processes 87, 237-247.