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

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.