Aryl hydrazides as linkers for solid phase synthesis which are cleavable under mild oxidative conditions

被引：82

作者：

Millington, CR ^{[1
]}

Quarrell, R ^{[1
]}

Lowe, G ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 39期

基金：

英国生物技术与生命科学研究理事会;

关键词：

linkers; oxidative cleavage; peptide synthesis; solid phase synthesis;

D O I：

10.1016/S0040-4039(98)01543-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an acid/base stable aryl hydrazide linker which is readily coupled to solid phase resins. Cleavage is specific and facile, requiring a copper (II) catalyst, base and a nucleophile to proceed. The conditions are compatible with all 20 proteinogenic amino acids and quantitative cleavage is achieved within 2 hours at 20 degrees C to give peptides with C-terminal acid, amide or ester functionalities. Aryl hydrazides also offer scope as simple "traceless" linkers. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7201 / 7204

页数：4

共 9 条

[1] Atherton E, 1989, SOLID PHASE SYNTHESI
[2] Fehling H., 1849, Justus Liebigs Ann. Chem., V72, P106, DOI DOI 10.1002/JLAC.18490720112
[3] KING DS, 1990, INT J PEPT PROT RES, V36, P255
[4] LOWE G, 1995, CHEM SOC REV, P309
[5] NEWBOLD BT, 1975, CHEM HYDRAZO AZO AZO, P542
[6] A SILICON-BASED LINKER FOR TRACELESS SOLID-PHASE SYNTHESIS
PLUNKETT, MJ
ELLMAN, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) : 6006 - 6007
[7] SEMENOV AN, 1995, INT J PEPT PROT RES, V45, P303
[8] Sucholeiki Irving, 1997, P119
[9] COMBINATORIAL SYNTHESIS - THE DESIGN OF COMPOUND LIBRARIES AND THEIR APPLICATION TO DRUG DISCOVERY
TERRETT, NK
GARDNER, M
GORDON, DW
KOBYLECKI, RJ
STEELE, J
[J]. TETRAHEDRON, 1995, 51 (30) : 8135 - 8173

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