Biomimetic formation of gramicidin S by dimerization-cyclization of pentapeptide precursor on solid support

Tetrahedron Letters

Volumn 47, Issue 48, 2006, Pages 8475-8478

  Tamaki, Makoto ^a   Honda, Kenji ^a   Kikuchi, Sho ^a   Ishii, Rie ^a  

^a TOHO UNIVERSITY   (Japan)

Author keywords

Biomimetic synthesis; Dimerization cyclization on solid phase; Gramicidin S; Oxime resin; Reaction mechanism

Indexed keywords

DIOXANE DERIVATIVE; GRAMICIDIN S; OXIME; PENTAPEPTIDE; RESIN;

ANTIMICROBIAL ACTIVITY; ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CYCLIZATION; DIMERIZATION; METHODOLOGY; NONHUMAN; PRECURSOR; RACEMIZATION; SOLID;

EID: 33750360856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.146     Document Type: Article

References (48)

1. Dubos R.J. J. Exp. Med. 70 (1939) 1-10
2. Gause G.F., and Brazhnikova M. Nature 154 (1944) 703
3. Battersby A.R., and Craig L.C. J. Am. Chem. Soc. 73 (1951) 1887-1888
4. Amino acid residues with no prefix have the l-configuration. The abbreviations for amino acids and peptides are in accordance with the rules of the IUPAC-IBU Nomenclature of Organic Chemistry; Rigaudy, J., Klesney, S. P., Eds.; Pergamon: Oxford, 1979.
5. Krätzschmar J., Krause M., and Maraheil M.A. J. Bacteriol. 171 (1989) 5422-5429
6. Kleinkauf H., and von Döhren H. Eur. J. Biochem. 192 (1990) 1-15
7. Turgay K., Krause M., and Marahaeil M.A. Mol. Micriobiol. 6 (1992) 529-546
8. Kleinkauf H., and von Döhren H. Eur. J. Biochem. 236 (1996) 335-351
9. von Döhren, Keller U., Vater J., and Zocher R. Chem. Rev. 97 (1997) 2675-2706
10. Marahiel M.A., Stachelhaus T., and Mootz H.D. Chem. Rev. 97 (1997) 2661-2674
11. Schwyzer R., and Sieber P. Helv. Chem. Acta. 41 (1958) 2186-2189
12. Izumiya N., Kato T., Aoyagi H., Waki M., and Kondo M. Synthetic Aspects of Biologically Active Cyclic Peptide-Gramicidin S and Tyrocidines (1979), Kodansha Ltd. and Wiley, Tokyo
13. Minemutsu Y., Waki M., Suwa K., Kato T., and Izumiya N. Tetrahedron Lett. 21 (1980) 2179-2180
14. Imazu S., Shimohigashi Y., Kodama H., Sakaguchi K., Waki M., Kato T., and Izumiya N. Int. J. Pept. Protein Res. 32 (1988) 298-306
15. Tamaki M., Takimoto M., Hayashi M., and Muramatsu I. Bull. Chem. Soc. Jpn. 62 (1989) 594-596
16. Tamaki M., Akabori S., and Muramatsu I. Bull. Chem. Soc. Jpn. 66 (1993) 3113-3115
17. Tamaki M., Akabori S., and Muramatsu I. J. Am. Chem. Soc. 115 (1993) 10492-10496
18. Tamaki M., Komiya M., Akabori S., and Muramatsu I. J. Chem. Soc., Perkin Trans. 1 14 (1997) 2045-2050
19. Tamaki M., Ishi R., Kikuchi S., and Watanabe E. J. Antibiotics 58 (2005) 293-295
20. Izumiya N., Kato T., and Waki M. Biopolymers 20 (1981) 1785-1791
21. Ji A.-Xm., and Bodansky M. Int. J. Pept. Protein Res. 22 (1983) 590-596
22. Klosteremyer H. Chem. Ber. 101 (1968) 2823-2831
23. Losse G., and Neubert K. Tetrahedron Lett. 15 (1970) 1267-1270
24. Ohno M., Kuromizu K., Ogawa H., and Izumiya N. J. Am. Chem. Soc. 93 (1971) 5251-5254
25. Sato K., Abe H., Kato T., and Izumiya N. Bull. Chem. Soc. Jpn. 50 (1977) 1999-2004
26. Aimoto S. Bull. Chem. Soc. Jpn. 61 (1988) 2220-2222
27. Ösapy G., Profit A., and Taylor J.W. Tetrahedron Lett. 31 (1990) 6121-6124
28. Xu M., Nishino N., Mihara H., Fujimoto T., and Izumiya N. Chem. Lett. (1992) 191
29. Wishart D.S., Kondejewski L.H., Semchuk P.D., and Hodges R.S. Lett. Pep. Sci. 3 (1996) 53
30. Andreu D., Ruiz S., Carreño C., Alsina J., Albericio F., Jiménez J.A., Figuera N., Herranz R., Garcia-López M.T., and González-Muńiz R. J. Am. Chem. Soc. 119 (1997) 10579-10586
31. Arai T., Maruo N., Sumida Y., Korosue C., and Nishino N. Chem. Commun. 16 (1999) 1503-1504
32. Qin C., Bu X., Wu X., and Guo Z. J. Comb. Chem. 5 (2003) 353
33. Bu X., Wu X., Wong K.M., Ng N.L., Mak C.K., Qin C., and Guo Z. J. Org. Chem. 69 (2004) 2681-2685
34. Trauger J.W., Kohi R.M., Mootz H.D., Marahiel M.A., and Walsh C.T. Nature 407 (2000) 215-218
35. Trauger J.W., Kohi R.M., and Walsh C.T. Biochemistry 40 (2001) 7092-7098
36. Kohi R.M., Trauger J.W., Schwazer D., Marahiel M.A., and Walsh C.T. Biochemistry 40 (2001) 7099-7108
37. Kohi R.M., Walsh C.T., and Burkart M.D. Nature 418 (2002) 658-661
38. Bu X., Wu X., Bu X., Xie G., and Guo Z. Org. Lett. 4 (2002) 2893-2895
39. Wu X., Bu X., Wong K.M., Yan W., and Guo Z. Org. Lett. 5 (2003) 1749-1752
40. Lin H., and Walsh C.T. J. Am. Chem. Soc. 126 (2004) 13998-14003
41. DeGrado W.F., and Kaiser E.T. J. Org. Chem. 45 (1980) 1295-1300
42. DeGrado W.F., and Kaiser E.T. J. Org. Chem. 47 (1982) 3258-3261
43. Nakagawa S.H., and Kaiser E.T. J. Org. Chem. 48 (1983) 678-685
44. Nakagawa S.H., and Kaiser E.T. J. Am. Chem. Soc. 107 (1985) 7087-7092
45. Mihara H., and Kaiser E.T. Science 242 (1988) 925-927
46. Sasaki T., Findeis M.A., and Kaiser E.T. J. Org. Chem. 56 (1991) 3159-3168
47. Gisin B.F., and Merrifield R.B. J. Am. Chem. Soc. 94 (1972) 3102-3106
48. Ösapay G., and Taylor J.W. J. Am. Chem. Soc. 112 (1990) 6046-6051