The synthesis of active and stable diaminopimelate analogues of the lantibiotic peptide lactocin S

Journal of the American Chemical Society

Volumn 134, Issue 4, 2012, Pages 2008-2011

  Ross, Avena C ^a   McKinnie, Shaun M K ^a   Vederas, John C ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVITY LEVELS; ANTIMICROBIAL COMPOUNDS; CLINICAL APPLICATION; GRAM-POSITIVE BACTERIUM; LANTHIONINES; LANTIBIOTICS; OXIDATIVE STABILITY; SOLID PHASE PEPTIDE SYNTHESIS;

AMINO ACIDS; BACTERIA; FOOD PRESERVATION; SULFUR;

PEPTIDES;

CARBENE; DIAMINOPIMELATE LACTOCIN S DERIVATIVE; DIAMINOPIMELIC ACID; LACTOCIN S; LANTHIONINE; LANTIBIOTIC; SULFUR; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG STABILITY; DRUG SYNTHESIS;

ANTI-BACTERIAL AGENTS; DIAMINOPIMELIC ACID; DOSE-RESPONSE RELATIONSHIP, DRUG; LACTOBACILLUS; LISTERIA MONOCYTOGENES; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; PEDIOCOCCUS; PEPTIDES;

EID: 84856489591     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211088m     Document Type: Article

References (33)

1. Willey, J. M.; van der Donk, W. A. Annu. Rev. Microbiol. 2007, 61, 477
2. Chatterjee, C.; Paul, M.; Xie, L.; van der Donk, W. A. Chem. Rev. 2005, 105, 633
3. Asaduzzaman, S. M.; Sonomoto, K. J. Biosci. Bioeng. 2009, 107, 475
4. McAuliffe, O.; Ross, R. P.; Hill, C. FEMS Microbiol. Rev. 2001, 25, 285
5. Twomey, D.; Ross, R. P.; Ryan, M.; Meaney, B.; Hill, C. Antonie van Leeuwenhoek 2002, 82, 165
6. Cotter, P. D.; Hill, C.; Ross, R. P. Curr. Protein Pept. Sci. 2005, 6, 61
7. Lee, M. V.; Ihnken, L. A. F.; You, Y. O.; McClerren, A. L.; van der Donk, W. A.; Kelleher, N. L. J. J. Am. Chem. Soc. 2009, 131, 12258
8. Bierbaum, G.; Sahl, H.-G. Curr. Pharm. Biotechnol. 2009, 10, 2
9. Breukink, E.; Wiedemann, I.; van Kraaij, C.; Kuipers, O. P.; Sahl, H.-G.; de Kruijff, B. Science 1999, 286, 2361
10. Breukink, E.; de Kruijff, B. Nat. Rev. Drug Discovery 2006, 5, 321
11. Martin, N. I.; Breukink, E. Future Microbiol. 2007, 2, 513
12. Wilson-Stanford, S.; Kalli, A.; Håkansson, K.; Kastrantas, J.; Orugunty, R. S.; Smith, L. Appl. Environ. Microbiol. 2009, 75, 1381
13. Ross, A. C.; Liu, H.; Pattabiraman, V. R.; Vederas, J. C. J. Am. Chem. Soc. 2010, 132, 462
14. Ross, A. C.; Vederas, J. C. J. Antibiot. 2011, 64, 27
15. Mustapa, M. F. M.; Harris, R.; Bulic-Subanovic, N.; Elliot, S. L.; Bregant, S.; Groussier, M. F. A.; Mould, J.; Schultz, D.; Chubb, N. A. L.; Gaffney, P. R. J.; Driscoll, P. C.; Tabor, A. B. J. Org. Chem. 2003, 68, 8185
16. Martin, N. I. J. Org. Chem. 2009, 74, 946
17. Cobb, S. L.; Vederas, J. C. Org. Biomol. Chem. 2007, 5, 1031
18. Narayan, R. S.; VanNieuwenhze, M. S. Org. Lett. 2005, 7, 2655
19. Paul, M.; van der Donk, W. A. Mini-Rev. Org. Chem. 2005, 2, 23
20. Mustapa, M. F. M.; Harris, R.; Esposito, D.; Chubb, N. A. L.; Mould, J.; Schultz, D.; Driscoll, P. C.; Tabor, A. B. J. Org. Chem. 2003, 68, 8193
21. Ghalit, N.; Reichwein, J. F.; Hilbers, H. W.; Breukink, E.; Rijkers, D. T. S.; Liskamp, R. M. J. ChemBioChem 2007, 8, 1540
22. Ghalit, N.; Rijkers, D. T. S.; Liskamp, R. M. J. J. Mol. Catal. A: Chem. 2006, 254, 68
23. Tabor, A. B. Org. Biomol. Chem. 2011, 9, 7606
24. Mothia, B.; Appleyard, A. N.; Wadman, S.; Tabor, A. B. Org. Lett. 2011, 13, 4216
25. Pattabiraman, V. R.; Stymiest, J. L.; Derksen, D. J.; Martin, N. I.; Vederas, J. C. Org. Lett. 2007, 9, 699
26. Pattabiraman, V. R.; McKinnie, S. M. K.; Vederas, J. C. Angew. Chem., Int. Ed. 2008, 47, 9472
27. Liu, H.; Pattabiraman, V. R.; Vederas, J. C. Org. Lett. 2009, 11, 5574
28. Mørtvedt, C. I.; Nissen-Meyer, J.; Sletten, K.; Nes, I. F. Appl. Environ. Microbiol. 1991, 57, 1829
29. Mørtvedt, C. I.; Nes, I. F. J. Gen. Microbiol. 1990, 136, 1601
30. Skaugen, M.; Nissen-Meyer, J.; Jung, G.; Stevanovic, S.; Sletten, K.; Abildgaard, C. I. M.; Nes, I. F. J. Biol. Chem. 1994, 269, 27183
31. Spantulescu, M. D.; Jain, R. P.; Derksen, D. J.; Vederas, J. C. Org. Lett. 2003, 5, 2963
32. Bregant, S.; Tabor, A. B. J. Org. Chem. 2005, 70, 2430
33. Zhu, X.; Schmidt, R. R. Eur. J. Org. Chem. 2003, 4069