Efficient solid-phase synthesis of peptides with tripodal side-chain bridges and optimization of the solvent conditions for solid-phase cyclizations

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2173-2176

  Zhang, Wentao ^a   Taylor, John W ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029947582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00220-1     Document Type: Article

References (14)

1. (a) Felix, A.M.; Heimer, E.P.; Wang C.T.; Lambros, T.J.; Fournier, A.; Mowles, T.F.; Maines, S.; Campbell, R.M.; Wegrzynski, B.B.; Toome, V.; Fry, D.; Madison, V.S. Int. J. Pept. Protein Res. 1988, 32, 441-454.
2. (b) Ösapay, G.; Taylor, J.W. J. Am. Chem. Soc., 1992, 114, 6966-6973.
3. (c) Ösapay, G.; Gulyás, J.; Profit, A. A.; Gulyás, E. S.; Taylor, J. W. Proc. 12th Amer. Peptide Symp.; Peptides: Chemistry and Biology Smith, J.A.; Rivier, J.E. Eds.; ESCOM, B.V., 1992, pp. 239-240.
4. Bracken, C.; Gulyas, J.; Taylor, J.W.; Baum, J. J. Am. Chem. Soc. 1994, 116, 6431-6432.
5. (a) Wu, B.; Taylor, J.W., manuscript submitted.
6. (b) Yu, C.; Taylor, J.W., manuscript submitted.
7. Jackson, D.Y.; King, D.S.; Chmielewski, J.; Singh, S.; Schultz, P.C. J. Am. Chem. Soc. 1991, 113, 9391-9392.
8. Kapurniotu, A.; Taylor, J.W. J. Med. Chem. 1995, 38, 836-847.
9. Fields, G.B.; Fields, C.G. J. Am. Chem. Soc. 1991, 113, 4202-4207.
10. 2O in 63% yield, based on Alloc-Dap(Fmoc)-OH, and confirmed by NMR and mass spectrometry.
11. 2O in 63% yield, based on Alloc-Dap(Fmoc)-OH, and confirmed by NMR and mass spectrometry.
12. 2O in 63% yield, based on Alloc-Dap(Fmoc)-OH, and confirmed by NMR and mass spectrometry.
13. Kates, S.A.; Sole, N.A.; Johnson, C.R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552.
14. All solvent mixtures are reported as volume ratios. Abbreviations: Alloc, allyloxycarbonyl; Boc, tert-butoxycarbonyl; BOP, benzotriazolyloxy-tris-(dimethylamino)phosphonium hexafluorophosphate; DAP, diaminopropionic acid; DCM, dichloromethane DIEA, N,N-diisopropylethylamine; Fmoc, fluorenylmethyloxycarbonyl; NMP, 1-methyl-2-pyrrolidinone; OA1, ally1 ester, OFm, fluorenylmethyl ester; TFA, trifluoroacetic acid. This research was supported by USPHS grant DA04197.