Alanine scan of [L-Dap2]ramoplanin A2 aglycon: Assessment of the importance of each residue

Journal of the American Chemical Society

Volumn 129, Issue 28, 2007, Pages 8747-8755

  Nam, Joonwoo ^a   Shin, Dongwoo ^a   Rew, Yosup ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE SCAN; ANTIMICROBIAL ACTIVITY;

ANTIBIOTICS; BIOSYNTHESIS; CELLS; COMPLEXATION; MOLECULAR STRUCTURE;

BACTERIA;

(2,3 DIAMINOPROPIONIC ACID) RAMOPLANIN A2 AGLYCON; AGLYCONE; ALANINE; POLYPEPTIDE ANTIBIOTIC AGENT; RAMOPLANIN; UNCLASSIFIED DRUG; AMINO ACID; ANTIINFECTIVE AGENT; DEPSIPEPTIDE; GLYCOPROTEIN; PEPTIDE LIBRARY; RAMOPLANIN A2;

AMINO ACID SEQUENCE; ARTICLE; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; REACTION ANALYSIS; SEQUENCE ANALYSIS; STAPHYLOCOCCUS AUREUS; STRUCTURE ANALYSIS; GENETICS; SITE DIRECTED MUTAGENESIS;

ALANINE; AMINO ACIDS; ANTI-BACTERIAL AGENTS; DEPSIPEPTIDES; GLYCOPROTEINS; MUTAGENESIS, SITE-DIRECTED; PEPTIDE LIBRARY;

EID: 34548380947     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068573k     Document Type: Article

References (51)

1. Walsh, C. T. Nature 2000, 406, 775.
2. (a) Pearson, H. Nature 2002, 418, 469.
3. (b) Review: von Nussbaum, F.; Brands, M.; Hinzen, B.; Weigand, S.; Häbich, D. Angew. Chem., Int. Ed. 2006, 45, 5072.
4. (a) Cavalleri, B.; Pagani, H.; Volpe, G.; Selva, E.; Parenti, F. J. Antibiot. 1984, 37, 309.
5. (b) Pallanza, R.; Berti, M.; Scotti, R.; Randisi, E.; Arioli, V. J. Antibiot. 1984, 37, 318.
6. (a) Ciabatti, R.; Kettenring, J. K.; Winters, G.; Tuan, G.; Zerilli, L.; Cavalleri, B. J. Antibiot. 1989, 42, 254.
7. (b) Kettenring, J. K.; Ciabatti, R.; Winters, G.; Tamborini, G.; Cavalleri, B. J. Antibiot. 1989, 42, 268.
8. Reviews: (c) Walker, S.; Chen, L.; Hu, Y.; Rew, Y.; Shin, D.; Boger, D. L. Chem. Rev. 2005, 105, 449.
9. (d) Parenti, F.; Ciabatti, R.; Cavalleri, B.; Kettenring, J. Drugs Exp. Clin. Res. 1990, 16, 451.
10. (e) McCafferty, D. G.; Cudic, P.; Frankel, B. A.; Barkallah, S.; Kruger, R. G.; Li, W. Biopolymers 2002, 66, 261.
11. (a) Review: Espersen, F. Curr. Opin. Anti-Infect. Invest. Drugs 1999, 1, 78.
12. (b) Montecalvo, M. A. J. Antimicrob. Chemother. 2003, 51 (Suppl. S3), iii31 .
13. (a) Somner, E. A.; Reynolds, P. E. Antimicrob. Agents Chemother. 1990, 34, 413.
14. (b) Review: Reynolds, P. E.; Somner, E. A. Drugs Exp. Clin. Res. 1990, 16, 385.
15. (c) Brötz, H.; Bierbaum, G.; Reynolds, P. E.; Sahl, H.-G. Eur. J. Biochem. 1997, 246, 193.
16. (d) Lo, M.-C.; Men, H.; Branstrom, A.; Helm, J.; Yao, N.; Goldman, R.; Walker, S. J. Am. Chem. Soc. 2000, 122, 3540.
17. (e) Lo, M.-C.; Helm, J. S.; Sarngadharan, G.; Pelczer, I.; Walker, S. J. Am. Chem. Soc. 2001, 123, 8640.
18. (f) Helm, J. S.; Chen, L.; Walker, S. J. Am. Chem. Soc. 2002, 124, 13970.
19. (g) Hu, Y.; Helm, J. S.; Chen, L.; Ye, X.-Y.; Walker, S. J. Am. Chem. Soc. 2003, 125, 8736.
20. Reviews: (a) Barna, J. C. J.; Williams, D. H. Annu. Rev. Microbiol. 1984, 38, 339.
21. (b) Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172.
22. (a) Cudic, P.; Kranz, J. K.; Behenna, D. C.; Kruger, R. G.; Tadesse, H.; Wand, A. J.; Veklich, Y. I.; Weisel, J. W.; McCafferty, D. G. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 7384.
23. (b) Cudic, P.; Behenna, D. C.; Kranz, J. K.; Kruger, R. G.; Wand, A. J.; Veklich, Y. I.; Weisel, J. W.; McCafferty, D. G. Chem. Biol. 2002, 9, 897.
24. Jones, R. N.; Barry, A. L. Diagn. Microbiol. Infect. Dis. 1989, 12, 279.
25. Kurz, M.; Guba, W. Biochemistry 1996, 35, 12570.
26. Skelton, N. J.; Harding, M. M.; Mortishire-Smith, R. J.; Rahman, S. K.; Williams, D. H.; Rance, M. J.; Ruddock, J. C. J. Am. Chem. Soc. 1991, 113, 7522.
27. (a) Higashide, E.; Hatano, K.; Shibata, M.; Nakazawa, K. J. Antibiot. 1968, 21, 126.
28. (b) Asai, M.; Muroi, M.; Sugita, N.; Kawashima, H.; Mizuno, K.; Miyake, A. J. Antibiot. 1968, 21, 138.
29. (c) Tsuchiya, K.; Takeuchi, Y. J. Antibiot. 1968, 21, 426.
30. (d) Hori, M.; Iwasaki, H.; Horii, S.; Yoshida, I.; Hongo, T. Chem. Pharm. Bull. 1973, 21, 1175.
31. (e) Iwasaki, H.; Horii, S.; Asai, M.; Mizuno, K.; Ueyanagi, J.; Miyake, A. Chem. Pharm. Bull. 1973, 21, 1184.
32. (f) Fang, X.; Tiyanont, K.; Zhang, Y.; Wanner, J.; Boger, D.; Walker, S. Mol. BioSyst. 2006, 2, 69.
33. Castiglione, F.; Marazzi, A.; Meli, M.; Colombo, G. Magn. Reson. Chem. 2005, 43, 603.
34. (a) Meyers, E.; Weisenborn, F. L.; Pansy, F. E.; Slusarchyk, D. S.; von Saltza, M. H.; Rathnum, M. L.; Parker, W. L. J. Antibiot. 1970, 23, 502.
35. (b) Linnett, P. E.; Strominger, J. L. Antimicrob. Agents Chemother. 1973, 4, 231.
36. (a) Jiang, W.; Wanner, J.; Lee, R. J.; Bounaud, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5288.
37. (b) Jiang, W.; Wanner, J.; Lee, R. J.; Bounaud, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 1877.
38. (c) Review: Boger, D. L. Med. Res. Rev. 2001, 21, 356-381.
39. 3, EtOAc) should be used to take advantage of the β-sheet preorganization. However, the linear substrates typically proved insoluble in such solvents. Consequently, variable amounts of DMF are added until the substrates were dissolved,
40. (b) Maplestone, R. A.; Cox, J. P. L.; Williams, D. H. FEBS Lett. 1993, 326, 95.
41. (a) Rich, D. H.; Bhatnagar, P.; Mathiaparanam, P.; Grant, J. A.; Tam, J. P. J. Org. Chem. 1978, 43, 296.
42. (b) 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.
43. Shin, D.; Rew, Y.; Boger, D. L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11977.
44. Rew, Y.; Shin, D.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2004, 126, 1041.
45. Chen, L.; Yuan, Y.; Helm, J. S.; Hu, Y.; Rew, Y.; Shin, D.; Boger, D. L.; Walker, S. J. Am. Chem. Soc. 2004, 126, 7462.
46. (a) Brötz, H.; Bierbaum, G.; Leopold, K.; Reynolds, P. E.; Sahl, H.-G. Antimicrob. Agents Chemother. 1998, 42, 154.
47. (b) Brötz, H.; Josten, M.; Wiedemann, I.; Schneider, U.; Gotz, F.; Bierbaum, G.; Sahl, H.-G. Mol. Microbiol. 1998, 30, 317.
48. Chen, Y.; Bilban, M.; Foster, C. A.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5431.
49. EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, HOAt = 1-hydroxy-7-azabenzotriazole, DEPBT = 3-(diethoxyphosphoryloxy)-1,2,3- benzotriazin-4(3H)-one, SES = 2-trimethylsilylethanesulfonyl, BCB = B-bromocatecholborane.
50. In contrast, removal of the aromatic chlorines from vancomycin diminished dimerization and altered its antimicrobial activity. See: (a) Harris, C. M.; Kannan, R.; Kopecka, H.; Harris, T. M. J. Am. Chem. Soc. 1985, 107, 6652.
51. (b) Gerhard, U.; Mackay, J. P.; Maplestone, R. A.; Williams, D. H. J. Am. Chem. Soc. 1993, 115, 232.