Practical method for the combinatorial synthesis of peptide aldehydes

被引：35

作者：

Hall, BJ

Sutherland, JD

机构：

[1] Cambridge Combinatorial Ltd, Merrifield Ctr, Cambridge CB1 3LQ, England

[2] Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(98)01374-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical strategy for solid phase synthesis of peptide aldehydes is described. An olefin linker is constructed using Wittig chemistry, after peptide synthesis ozonolylic treatment of the linker and subsequent workup with dimethyl sulphide results in facile isolation of peptide aldehydes. The principle is demonstrated by synthesis of a 3x3x3 array of 27 tripeptide aldehydes. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6593 / 6596

页数：4

共 9 条

[1] DE FRUTOS P, 1991, TETRAHEDRON LETT, V32, P541
[2] Pyridazinodiazepines as a high-affinity, P-2-P-3 peptidomimetic class of interleukin-1 beta-converting enzyme inhibitor
Dolle, RE
Prasad, CVC
Prouty, CP
Salvino, JM
Awad, MMA
Schmidt, SJ
Hoyer, D
Ross, TM
Graybill, TL
Speier, GJ
Uhl, J
Miller, BE
Helaszek, CT
Ator, MA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (13) : 1941 - 1946
[3] IMPROVED SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE ALDEHYDES
FEHRENTZ, JA
PARIS, M
HEITZ, A
VELEK, J
LIU, CF
WINTERNITZ, F
MARTINEZ, J
[J]. TETRAHEDRON LETTERS, 1995, 36 (43) : 7871 - 7874
[4] FRECHET JM, 1971, J AM CHEM SOC, V93, P492
[5] CONFIGURATIONAL STABILITY OF N-PROTECTED ALPHA-AMINO ALDEHYDES
LUBELL, WD
RAPOPORT, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (01) : 236 - 239
[6] ON THE DOUBLE-BOND ISOSTERE OF THE PEPTIDE-BOND - PREPARATION OF MODIFIED DI-PEPTIDE AND TRI-PEPTIDE INCORPORATING PROLINE AND ALANINE ANALOGS
MILES, NJ
SAMMES, PG
KENNEWELL, PD
WESTWOOD, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2299 - 2305
[7] Use of ozonolysis in the synthesis of C-terminal peptide aldehydes on solid support
Pothion, C
Paris, M
Heitz, A
Rocheblave, L
Rouch, F
Fehrentz, JA
Martinez, J
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7749 - 7752
[8] SARRUBI E, 1992, FEBS LETT, V319, P253
[9] Small peptidic aldehyde inhibitors of human rhinovirus 3C protease
Shepherd, TA
Cox, GA
McKinney, E
Tang, J
Wakulchik, M
Zimmerman, RE
Villarreal, EC
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (23) : 2893 - 2896

← 1 →