An improved solid-phase methodology for the synthesis of putative hexa- and heptapeptide intermediates in vancomycin biosynthesis

Organic and Biomolecular Chemistry

Volumn 3, Issue 7, 2005, Pages 1233-1239

  Li, Dong Bo ^a   Robinson, John A ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; BIOSYNTHESIS; CATALYSIS; CRYSTALLIZATION; ENZYMES; GENES; REACTION KINETICS; RESINS; SYNTHESIS (CHEMICAL);

HEPTAPEPTIDES; NON-RIBOSOMAL PEPTIDE SYNTHETASE (NRPS); OXIDATIVE PHENOL COUPLING REACTIONS (OPCR); VANCOMYCIN;

AMINO ACIDS;

OLIGOPEPTIDE; VANCOMYCIN;

ARTICLE; BIOSYNTHESIS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; VANCOMYCIN;

EID: 17444424979     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418908f     Document Type: Article

References (27)

1. B. K. Hubbard and C. T. Walsh, Angew. Chem. Int. Ed., 2003, 42, 730-765.
2. R. D. Sussmuth and W. Wohlleben, Appl. Microbiol. Biotechnol., 2004, 63, 344-350.
3. D. H. Williams and B. Bardsley, Angew. Chem. Int. Ed., 1999, 38, 1172-1193.
4. J. C. J. Barna and D. H. Williams, Annu. Rev. Microbiol., 1984, 38, 339-357.
5. R. Stadler and M. H. Zenk, J. Biol. Chem., 1993, 268, 823-831.
6. P. F. X. Kraus and T. M. Kutchan, Proc. Natl. Acad. Sci. U. S. A., 1995, 92, 2071-2075.
7. R. Gerardy and M. H. Zenk, Phytochemistry, 1993, 32, 79-86.
8. A. Nasreen, M. Rueffer and M. H. Zenk, Tetrahedron Lett., 1996, 45, 8161-8164.
9. A. M. A. van Wageningen, P. N. Kirkpatrick, D. H. Williams, B. R. Harris, J. K. Kershaw, N. J. Lennard, M. Jones, S. J. M. Jones and P. J. Solenberg, Chem. Biol., 1998, 5, 155-162.
10. S. Pelzer, R. D. Süssmuth, D. Heckmann, J. Recktenwald, P. Huber, G. Jung and W. Wohlleben, Antimicrob. Agents Chemother., 1999, 43, 1565-1573.
11. T.-L. Li, F. Huang, S. F. Haydock, T. Mironenko, P. F. Leadlay and J. B. Spencer, Chem. Biol., 2004, 11, 107-119.
12. M. Sosio, A. Bianchi, E. Bossi and S. Donadio, Antonie van Leeuwenhoek, 2000, 78, 379-384.
13. M. Sosio, H. Kloosterman, A. Bianchi, d. P. L. Dijkhuizen and S. Donadio, Microbiology, 2004, 150, 95-102.
14. H.-T. Chiu, B. K. Hubbard, A. N. Shah, J. Eide, R. A. Fredenburg, C. T. Walsh and C. Khosla, Proc. Natl. Acad. Sci. U.S.A., 2001, 98, 8548-8553.
15. J. Pootoolal, M. G. Thomas, C. G. Marshall, J. M. Neu, B. K. Hubbard, C. T. Walsh and G. D. Wright, Proc. Natl. Acad. Sci. U. S. A., 2002, 99, 8962-8967.
16. M. Sosio, S. Stinchi, F. Beltrametti, A. Lazzarini and S. Donadio, Chem. Biol., 2003, 10, 541-549.
17. K. Zerbe, O. Pylypenko, F. Vitali, W. W. Zhang, S. Rouse, M. Heck, J. W. Vrijbloed, D. Bischoff, B. Bister, R. D. Süssmuth, S. Pelzer, W. Wohlleben, J. A. Robinson and I. Schlichting, J. Biol. Chem., 2002, 277, 47476-47485.
18. O. Pylypenko, F. Vitali, K. Zerbe, J. A. Robinson and I. Schlichting, J. Biol. Chem., 2003, 278, 46727-46733.
19. D. Bischoff, S. Pelzer, B. Bister, G. J. Nicholson, S. Stockert, M. Schirle, W. Wohlleben, G. Jung and R. D. Süssmuth, Angew. Chem. Int. Ed., 2001, 40, 4688-4691.
20. D. Bischoff, S. Pelzer, A. Höltzel, G. J. Nicholson, S. Stockert, W. Wohlleben, G. Jung and R. D. Süssmuth, Angew. Chem. Int. Ed., 2001, 40, 1693-1696.
21. R. D. Süssmuth, S. Pelzer, G. Nicholson, T. Walk, W. Wohlleben and G. Jung, Angew. Chem. Int. Ed., 1999, 38, 1976-1979.
22. K. Zerbe, K. Woithe, D. B. Li, F. Vitali, L. Bigler and J. A. Robinson, Angew. Chem. Int. Ed., 2004, 43, 6709-6713.
23. F. Vitali, K. Zerbe and J. A. Robinson, Chem. Commun., 2003, 2718-2719.
24. E. Freund, F. Vitali, A. Linden and J. A. Robinson, Helv. Chim. Acta, 2000, 83, 2572-2579.
25. E. Freund and J. A. Robinson, Chem. Commun., 1999, 2509-2510.
26. D. A. Evans and A. E. Weber, J. Am. Chem. Soc., 1987, 109, 7151-7157.
27. S. D. Erickson, J. A. Simon and W. C. Still, J. Org. Chem., 1993, 58, 1305-1308.