Solid-phase synthesis of lysobactin (katanosin B): Insights into structure and function

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2730-2733

  Hall, Edward A ^a   Kuru, Erkin ^a   Vannieuwenhze, Michael S ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DEPSIPEPTIDE; LYSOBACTIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SOLID PHASE SYNTHESIS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; DEPSIPEPTIDES; MOLECULAR STRUCTURE; SOLID-PHASE SYNTHESIS TECHNIQUES;

EID: 84861796324     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300926d     Document Type: Article

References (24)

1. Shoji, J.; Hinoo, H.; Matsumoto, K.; Hattori, T.; Yoshida, T.; Matsuura, S.; Kondo, E. J. Antibiot. 1988, 41, 713-718
2. O'Sullivan, J.; McCullough, J. E.; Tymiak, A. A.; Kirsch, D. R.; Trejo, W. H.; Principe, P. A. J. Antibiot. 1988, 1740-1744
3. Bonner, D. P.; O'Sullivan, J.; Tanaka, S. K.; Clark, J. M.; Whitney, R. R. J. Antibiot. 1988, 1745-1751
4. von Nussbaum, F.; Anlauf, S.; Benet-Buchholz, J.; Häbich, D.; Köbberling, J.; Musza, L.; Telser, J.; Rübsamen-Waigmann, H.; Brunner, N. A. Angew. Chem., Int. Ed. 2007, 2039-2042
5. von Nussbaum, F.; Anlauf, S.; Koebberling, J.; Telser, J.; Haebich, D. (Aicuris G.m.b.H. & Co. K.-G., Germany). Procedure for synthesis of cyclic depsipeptides such as Lysobactin via peptide fragment assembly and intramolecular cyclization. DE102006018250A1, 2007.
6. von Nussbaum, F.; Brunner, N.; Endermann, R.; Fuerstner, C.; Hartmann, E.; Paulsen, H.; Ragot, J.; Schiffer, G.; Schuhmacher, J.; Svenstrup, N.; Telser, J.; Anlauf, S.; Bruening, M.-A. (Bayer Healthcare AG). Synthesis of lysobactin derivs. for use as antibacterial agents in the treatment or prevention of disease. DE102004053407A1, 2006.
7. Guzman-Martinez, A.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 2007, 129, 6017-6021
8. Rich, D. H.; Bhatnagar, P.; Mathiaparanam, P.; Grant, J. A.; Tam, J. P. J. Org. Chem. 1978, 43, 296-302
9. Brady, S. F.; Varga, S. L.; Freidinger, R. M.; Schwenk, D. A.; Mendlowski, M.; Holly, F. W.; Veber, D. F. J. Org. Chem. 1979, 44, 3101-3105
10. Birch, D.; Hill, R. R.; Jeffs, G. E.; North, M. Chem. Commun. 1999, 941-942
11. Elliott, D. F. J. Chem. Soc. 1949, 589-594
12. Markowski, P. J. J. Pept. Sci. 2005, 11, 60-64
13. Guzman-Martinez, A.; VanNieuwenhze, M. S. Synlett 2007, 10, 1513-1516
14. Makino, K.; Okamoto, N.; Hara, O.; Hamada, Y. Tetrahedron: Asymmetry 2001, 12, 1757-1762
15. Li, H.; Jiang, X.; Ye, Y.-h.; Fan, C.-X.; Romoff, T.; Goodman, M. Org. Lett. 1999, 1 (1) 91-93
16. Ye, Y.-H.; Li, H.; Jiang, X. Biopolymers 2005, 80, 172-178
17. Albericio, F.; Thieriet, N.; Alsina, J.; Giralt, E.; Guibe, F. Tetrahedron Lett. 1997, 38, 7275-7278
18. Egner, J. E.; Bradley, M. Tetrahedron 1997, 53, 14021-14030
19. Tung, R. D.; Rich, D. H. J. Am. Chem. Soc. 1985, 107, 4342-4343
20. Colucci, W. J.; Tung, R. D.; Petri, J. A.; Rich, D. H. J. Org. Chem. 1990, 55, 2895-2903
21. Lysobactin is an inhibitor of the transglycosylation reaction in the bacterial cell wall biosynthetic pathway: Maki, H.; Miura, K.; Yamano, Y. Antimicrob. Agents Chemother. 2001, 45 (6) 1823-1827
22. Bhakdi, S.; Martin, E. Infect. Immun. 1991, 59, 2955-2962
23. Virto, R.; Manas, P.; Alvarez, I.; Condon, S.; Raso, J. Appl. Environ. Microb. 2005, 71, 5022-5028
24. Ruhr, E.; Sahl, H. G. Antimicrob. Agents Chemother. 1985, 27, 841-845