Solid-phase total synthesis of polymyxin B1

Journal of Peptide Research

Volumn 53, Issue 5, 1999, Pages 501-506

  Sharma, Sushil K ^a   Wu, A D ^a   Chandramouli, N ^a   Fotsch, C ^a,b   Kardash, G ^a   Bair, K W ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^b AMGEN INC   (United States)

Author keywords

Fmoc Dab(Dde); Polymyxin B1; S (+) 6 methyloctane 1 carboxylic acid; Solid phase synthesis

Indexed keywords

POLYMYXIN B;

ARTICLE; DRUG CONFORMATION; DRUG DETERMINATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MASS SPECTROMETRY; MODELS, MOLECULAR; POLYMYXIN B; POLYMYXINS;

EID: 0033036951     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1034/j.1399-3011.1999.00045.x     Document Type: Article

References (42)

1. Stansly, P.G., Shepard, R.G. & White, H.J. (1947) Polymyxin: a new chemotherapeutic agent. Bull. Johns Hopkins Hosp. 81, 43-54.
2. Ainsworth, G.C., Brown, A.M. & Brownlee, G. (1947) 'Aerosporin', an antibiotic produced by Bacillus aerosporus Greer. Nature 160, 263.
3. Benedict, R.G. & Langlykke, A.F. (1947) Antibiotic activity of Bacillus polymyxa. J. Bact. 54, 24-25.
4. Jones, T.S.G. (1948) The chemical nature of 'Aerosporin'. Biochem. J. 42, 35.
5. Long, P.H. (1949) The present status of polymyxin, chloromycetin, and auromycin. Am. J. Pharm. 121, 64-75.
6. Moore, R.A., Bates, N.C. & Hancock, R.E.W. (1986) Interaction of polycationic antibiotics with Pseudomonas aeruginosa liposaccharide and lipid A studied by using dansyl-polymyxin. Antimicrob. Agents Chemother. 29, 496-500.
7. Craig, W.A., Turner, J.H. & Kunin, C.M. (1974) Prevention of the generalized Schwartzman reaction and endotoxin lethality by polymyxin B localized in tissues. Infect. Immun. 10, 287-292.
8. From, A.H.L., Fong, J.S.C. & Good, R.A. (1979) Polymyxin B sulphate modification of bacterial endotoxin: effects on the development of endotoxin shock in dogs. Infect. Immun. 23, 660-664.
9. Hughes, B., Madan, B.R. & Parratt, J.R. (1981) Polymyxin B sulfate protects cats against the haemodynamic and metabolic effects of E. coli endotoxin. Br. J. Pharmacol. 74, 701-707.
10. Jacobs, D.M. & Morrison, D.C. (1977) Inhibition of the mitogenic response to liposaccharide (LPS) in mouse spleen cells by polymyxin B. J. Immunol. 118, 21-27.
11. Corrigan, J.J. & Kiernat, J.F. (1979) Effect of polymyxin B sulphate on endotoxin activity in a Gram-negative septicemia model. Pediat. Res. 13, 48-51.
12. Flynn, P.M., Shenep, J.L., Stokes, D.C., Fairclough, D. & Hildner, W.K. (1987) Polymyxin B moderates acidosis and hypertension in established experimental Gram-negative septicemia. J. Infect. Dis. 156, 706-712.
13. Walterspiel, J.W., Kaplan, S.L. & Mason, E.O. (1986) Protective effect of subinhibitory polymyxin B alone and in combination with ampicillin for overwhelming Hemophilus influenzae type B infection in the infant rat: Evidence for in vivo and in vitro release of free endotoxin after ampicillin treatment. Pediat. Res. 20, 237-241.
14. Meek, M., Munster, A.M., Winchurch, R.A. & Dickerson, C. (1991) The Baltimore Sepsis Scale: Measurement of sepsis in patients with burns using a new scoring system. J. Burn Care Rehabil. 12, 564-568 (See also refs. 7-9).
15. Wilkinson, S. & Lowe, L.A. (1964) Structure of polymyxin B1. Nature 204, 1211.
16. Storm, D.R., Rosenthal, K.S. & Swanson, P.E. (1977) Polymyxin and related peptide antibiotics. Ann. Rev. Biochem. 46, 723-763.
17. Srinivasa, B.R. & Ramachandran, L.K. (1979) The polymyxins. J. Sci. Ind. Res. 38, 695-709.
18. Morozova, E.A. & Zewail, M.A. (1970) Synthesis of the heptapeptide of the cyclopeptide part of polymyxin B. Khim. Prir. Soedin. 6, 359-361.
19. Studer, R.O. & Lergier, W. (1970) Polymyxin syntheses. XXII. Synthesis of polymyxin D1. Helv. Chim. Acta 53, 929-937.
20. Oksenoit, E.S., Morozova, E.A., Gorbacheva, E.N. & Fokina, E.E. (1969) Synthesis of a fragment of the lysine analog of polymyxin M. Hydrazide of the protected tetrapeptide. Vestn. Mosk. Univ., Khim. 24, 119-120.
21. Zewail, M.A. & Morozova, E.A. (1971) Synthesis of a heptapeptide-protected lysine analog of the cyclopeptide part of polymyxin D on a resin. Vestn. Mosk. Univ., Khim. 12, 246-248.
22. Oksenoit, E.S., Morozova, E.A., Gorbacheva, E.N. & Fokina, E.E. (1969) Synthesis of a fragment of a lysine analog of polymyxin M. Zh. Obshch. Khim. 39, 1654-1658.
23. Zewail, M.A. (1977) Synthesis of heptapeptide-protected lysine-valine analog of cyclopeptide part of polymyxin B by solid-phase method. Ind. J. Chem., Sect. B 15B, 131-132.
24. Zewail, M.A. & Morozova, E.A. (1970) Synthesis of a heptapeptide, the protected lysine analog of the cyclopeptide part of polymyxin E, by a solid-phase method. Zh. Obshch. Khim. 40, 2760-2763.
25. Salem, E.M., Fedosceva, N.V. & Silacv, A.B. (1969) Chemistry of polymyxin M. XV. Synthesis of analogs. Preparation of cyclic peptides containing L-alpha, gamma-diaminobutyric acid. Zh. Obshch. Khim. 39, 2541-2545.
26. Morozova, E.A., Zewail, M.A. & Zhukora, G.F. (1970) Synthesis of a fragment of the lysine analog of polymyxin M on a polymer. Zh. Obshch. Khim. 40, 1376-1379.
27. Morozova, E.A., Okscoit, E.S. & Gorbacheva, E.N. (1968) Synthesis of a fragment of the lysine analog of polymyxin M. Zh. Obshch. Khim. 38, 2647-2648.
28. Oksenoit, E.S., Morozova, E.A. & Gorbacheva, E.N. (1969) Synthesis of open-chain protected decapeptide, a lysine analog of polymyxin M. Vestn. Mosk. Univ., Khim. 24, 113-115.
29. Salem, E.M. & El-Gammal, A.A. (1980) Synthesis of pelargonoyl-cyclic decapeptide analog of the antibiotic polymyxin B1. Pharmazie 35, 540-541.
30. Salem, E.M. (1980) Solid-phase synthesis of a cyclic decapeptide, analog of the antibiotic polymyxin M. Pharmazie 35, 761-763.
31. Morozova, E.A., Oksenoit, E.S. & Grava, I. (1967) Synthesis of a fragment of a polymyxin M lysine analog. Zh. Obshch. Khim. 37, 1764-1766.
32. Morozova, E.A., Oksenoit, E.S. & Borovikova, V.P. (1967) Synthesis of fragment of the lysine analog of polymyxin M. Vestn. Mosk. Univ., Set. 2: Khim, 22, 115-117.
33. Trezeciak, A. & Bannwarth, W. (1992) Synthesis of 'head-to-tail' cyclized peptides on solid support by Fmoc chemistry. Tetrahedron Lett. 33, 4557-4560.
34. Schnolzer, M., Alewood, P., Jones, A., Alewood, D. & Kent, S.B. (1992) In situ neutralization in Boc-chemistry solid-phase peptide synthesis. Int. J. Peptide Protein Res. 40, 180-193.
35. Kates, S.A., Sole, N.A., Johnson, C.R., Hudson, D., Barany, G. & Albericio, F. (1993) A novel, convenient, three-dimensional orthogonal strategy for solid-phase synthesis of cyclic peptides. Tetrahedron Lett. 34, 1549-1552.
36. Akaji, K., Nishiuchi, H. & Kiso, Y. (1995) Synthesis of human endothelin-1 by regioselective disulfide formation using the silyl chloride sulfoxide system. Tetrahedron Lett. 36, 1875-1878.
37. Lee, J., Griffin, J.H. & Nicas, T.I. (1996) Solid-phase total synthesis of bacitracin. J. Org. Chem. 61, 3983-3986.
38. Bycroft, B.W., Chan, W.C., Chhabra, S.R. & Hone, N.D. (1993) A novel lysine-protecting procedure for continuous flow solid-phase synthesis of branched peptides. J. Chem. Soc., Chem. Commun. 778-779.
39. Bycroft, B.W., Chan, W.C., Hone, N.D., Millington, S. & Nash, I.A. (1994) Synthesis of spider toxins nephilatoxin-9 and -11 by a novel solid-phase strategy. J. Amer. Chem. Soc. 116, 7415-7416.
40. Akhrem, A.A., Lakhvich, F.A., Budai, S.I., Khlebnicova, T.S. & Petrusevich, I.I. (1978) A new simple synthesis of 2-acylcyclohexane-1,3-dione. Synthesis 925-927.
41. Kraphco, A.P. (1982) Synthetic applications of dealkoxycarbonylation of malonate esters, β-keto esters, α-cyano esters and related compounds in dipolar aprotic media-Part 1. Synthesis 805.
42. Crombie, L. & Harper, S.H. (1950) Synthesis and configuration of (+)-6-methyloctanoic acid, a degradation product of the polymyxins. J. Chem. Soc. 2685-2689.