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
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
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