ARYL HYDRAZIDES AS LINKERS FOR SOLID-PHASE SYNTHESIS WHICH ARE CLEAVABLE UNDER MILD OXIDATIVE CONDITIONS

Citation
Cr. Millington et al., ARYL HYDRAZIDES AS LINKERS FOR SOLID-PHASE SYNTHESIS WHICH ARE CLEAVABLE UNDER MILD OXIDATIVE CONDITIONS, Tetrahedron letters, 39(39), 1998, pp. 7201-7204
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
39
Issue
39
Year of publication
1998
Pages
7201 - 7204
Database
ISI
SICI code
0040-4039(1998)39:39<7201:AHALFS>2.0.ZU;2-X
Abstract
We have developed an acid/base stable aryl hydrazide linker which is r eadily 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 an d quantitative cleavage is achieved within 2 hours at 20 degrees C to give peptides with C-terminal acid, amide or ester functionalities. Ar yl hydrazides also offer scope as simple ''traceless'' linkers. (C) 19 98 Elsevier Science Ltd. All rights reserved.