The synthesis of the cyclic antibacterial peptide Kawaguchipeptin B on 11 different DVB cross-linked PS resins

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5135-5139

  Rana, Sunil ^a   Dubuc, Julien ^a   Bradley, Mark ^a   White, Peter ^b  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b Calbiochem Novabiochem UK Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; DIPEPTIDE; ESTER DERIVATIVE; KAWAGUCHIPEPTIN B; POLYSTYRENE; RESIN; SOLVENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CROSS LINKING; CYCLIZATION; DRUG ISOLATION; DRUG SYNTHESIS; MICROCYSTIS AERUGINOSA; PEPTIDE SYNTHESIS;

MICROCYSTIS AERUGINOSA;

EID: 0034709616     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00754-1     Document Type: Article

References (17)

1. Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
2. Terrett, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron 1995, 51, 8135-8173.
3. Balkenhohl, F.; Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288-2337.
4. Blackburn, C. Biopolymers 1998, 47, 311-351.
5. Ishida, K.; Matsuda, H.; Murakami, M.; Yamaguchi, K. J. Nat. Prod. 1997, 60, 724-726.
6. tBu)-OH, Fmoc-Trp(Boc)-OH, Fmoc-Asn-OH, Fmoc-Asn-OH, Fmoc-Asp-OH].
7. Rink, H. Tetrahedron Lett. 1987, 28, 3787-3790.
8. Waldmann, H.; Kunz, H. Liebigs Ann. Chem. 1983, 1712-1725.
9. Sarin, V.K.; Kent, B.H.; Tam, J.P.; Merrifield, R.B. Anal. Biochem. 1981, 117, 147-157.
10. Kates, S.A.; Sole, N.A.; Johnson, C.R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron 1993, 34, 1549-1552, Marsh, I.R.; Teague, S.; Bradley, M. J. Org. Chem. 1997, 62, 6199-6203.
11. Kates, S.A.; Sole, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron 1993, 34, 1549-1552, Marsh, I.R.; Teague, S.; Bradley, M. J. Org. Chem. 1997, 62, 6199-6203.
12. Fields, G.B.; Noble, R.L. Int. J. Pept. Protein Res. 1990, 35, 161-214.
13. Analysis on a Hewlett Packard Chem Station; 150×3 mm Reverse Phase column, gradient 0-50% MeCN over 70 min, retention time 58.2 min.
14. δ), 1.352; 1.628; 1.866; 1.523.
15. +).
16. There are a number of variables which must be considered when altering the cross-linking ratios (Table 1). Thus the relative amounts of styrene, DVB and chloromethyl styrene and their relative incorporation ratios all need to be considered. In the present examples the incorporation of chloromethylstyrene used in the polymerisation mixtures was such as to give a real loading of 0.5 mmols/g. Thus, a typical protocol would be styrene (14.7 mL), DVB (desired% cross-linking×0.24), chloromethylstyrene (2.4 mL), PVA (2.5 g, 87-89% hydrolyzed, Mr 85-150 Kda) and benzoyl peroxide (0.25 g) suspended in water (1000 ml) at 80°C.
17. 2O, removed in vacuo), followed by the addition of the new solvent as above.