Mechanism of the C5 stereoinversion reaction in the biosynthesis of carbapenem antibiotics

Science

Volumn 343, Issue 6175, 2014, Pages 1140-1144

  Chang, Wei Chen ^a   Guo, Yisong ^a,c   Wang, Chen ^a   Butch, Susan E ^a   Rosenzweig, Amy C ^b   Boal, Amie K ^a,b   Krebs, Carsten ^a   Bollinger Jr , J Martin ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

^c CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENEM; HYDROGEN; TYROSINE; CARBAPENEM DERIVATIVE; ENZYME;

AMINO ACID; ANTIBIOTICS; BIOPHYSICS; CATALYSIS; ENZYME ACTIVITY; HYDROGEN; OXIDATION; RADICAL; SUBSTRATE;

ARTICLE; BIOPHYSICS; BIOSYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; TURNOVER TIME; CATALYSIS; CHEMISTRY; ENZYMOLOGY; ESCHERICHIA COLI; GENETICS; PECTOBACTERIUM CAROTOVORUM; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CARBAPENEMS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; ENZYMES; ESCHERICHIA COLI; HYDROGEN; OXIDATION-REDUCTION; PECTOBACTERIUM CAROTOVORUM; STEREOISOMERISM; TYROSINE;

EID: 84896781761     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1248000     Document Type: Article

References (44)

1. R. P. Elander, Appl. Microbiol. Biotechnol. 61, 385-392 (2003).
2. R. B. Hamed et al., Nat. Prod. Rep. 30, 21-107 (2013).
3. S. J. Coulthurst, A. M. Barnard, G. P. Salmond, Nat. Rev. Microbiol. 3, 295-306 (2005).
4. J. S. Bradley et al., Int. J. Antimicrob. Agents 11, 93-100 (1999).
5. Nature 495, 141 (2013).
6. J. S. Kahan et al., J. Antibiot. (Tokyo) 32, 1-12 (1979).
7. W. L. Parker et al., J. Antibiot. (Tokyo) 35, 653-660 (1982).
8. S. J. McGowan et al., Mol. Microbiol. 22, 415-426 (1996).
9. A. L. Demain, R. P. Elander, Antonie van Leeuwenhoek 75, 5-19 (1999).
10. R. F. Li, A. Stapon, J. T. Blanchfield, C. A. Townsend, J. Am. Chem. Soc. 122, 9296-9297 (2000).
11. B. Gerratana, S. O. Arnett, A. Stapon, C. A. Townsend, Biochemistry 43, 15936-15945 (2004).
12. R. B. Hamed, J. Mecinović, C. Ducho, T. D. Claridge, C. J. Schofield, Chem. Commun. 46, 1413-1415 (2010).
13. B. Gerratana, A. Stapon, C. A. Townsend, Biochemistry 42, 7836-7847 (2003).
14. A. Stapon, R. Li, C. A. Townsend, J. Am. Chem. Soc. 125, 8486-8493 (2003).
15. R. B. Woodward, Philos. Trans. R. Soc. Lond. B Biol. Sci. 289, 239-250 (1980).
16. A. Nangia, K. Biradha, G. R. Desiraju, J. Chem. Soc. Perk. Trans. 2, 943 (1996).
17. R. B. Hamed, E. T. Batchelar, J. Mecinović, T. D. Claridge, C. J. Schofield, ChemBioChem 10, 246-250 (2009).
18. R. B. Hamed et al., Nat. Chem. 3, 365-371 (2011).
19. R. B. Hamed et al., J. Am. Chem. Soc. 134, 471-479 (2012).
20. M. J. Bodner, R. M. Phelan, M. F. Freeman, R. Li, C. A. Townsend, J. Am. Chem. Soc. 132, 12-13 (2010).
21. R. P. Hausinger, Crit. Rev. Biochem. Mol. Biol. 39, 21-68 (2004).
22. C. Krebs, D. Galonić Fujimori, C. T. Walsh, J. M. Bollinger Jr., Acc. Chem. Res. 40, 484-492 (2007).
23. E. I. Solomon et al., Chem. Rev. 100, 235-350 (2000).
24. M. Costas, M. P. Mehn, M. P. Jensen, L. Que Jr., Chem. Rev. 104, 939-986 (2004).
25. M. Topf et al., J. Am. Chem. Soc. 126, 9932-9933 (2004).
26. T. Borowski, E. Broclawik, C. J. Schofield, P. E. M. Siegbahn, J. Comput. Chem. 27, 740-748 (2006).
27. R. M. Phelan, B. J. DiPardo, C. A. Townsend, ACS Chem. Biol. 7, 835-840 (2012).
28. R. M. Phelan, C. A. Townsend, J. Am. Chem. Soc. 135, 7496-7502 (2013).
29. J. Zhou et al., J. Am. Chem. Soc. 123, 7388-7398 (2001).
30. J. M. Bollinger Jr., C. Krebs, J. Inorg. Biochem. 100, 586-605 (2006).
31. J. M. Bollinger Jr. et al., Methods Enzymol. 258, 278-303 (1995).
32. H. R. Pfaendler, J. Gosteli, R. B. Woodward, G. Rihs, J. Am. Chem. Soc. 103, 4526-4531 (1981).
33. M. C. Sleeman et al., ChemBioChem 5, 879-882 (2004).
34. B. W. Bycroft, S. R. Chhabra, J. Chem. Soc. Chem. Commun. 423 (1989).
35. A. Avenoza, J. I. Barriobero, J. H. Busto, J. M. Peregrina, J. Org. Chem. 68, 2889-2894 (2003).
36. I. J. Clifton et al., J. Biol. Chem. 278, 20843-20850 (2003).
37. L. M. Hoffart, E. W. Barr, R. B. Guyer, J. M. Bollinger Jr., C. Krebs, Proc. Natl. Acad. Sci. U.S.A. 103, 14738-14743 (2006).
38. D. P. Galonić, E. W. Barr, C. T. Walsh, J. M. Bollinger Jr., C. Krebs, Nat. Chem. Biol. 3, 113-116 (2007).
39. M. L. Matthews et al., Biochemistry 48, 4331-4343 (2009).
40. M. L. Matthews et al., Proc. Natl. Acad. Sci. U.S.A. 106, 17723-17728 (2009).
41. J. C. Price, E. W. Barr, B. Tirupati, J. M. Bollinger Jr., C. Krebs, Biochemistry 42, 7497-7508 (2003).
42. J. M. Bollinger Jr., J. C. Price, L. M. Hoffart, E. W. Barr, C. Krebs, Eur. J. Inorg. Chem. 2005, 4245-4254 (2005).
43. K. P. McCusker, J. P. Klinman, Proc. Natl. Acad. Sci. U.S.A. 106, 19791-19795 (2009).
44. J. T. Groves, J. Chem. Educ. 62, 928 (1985).