Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis

…, GH Müller, M Lehnig, H Waldmann

Index: Voelkert, Martin; Koul, Surrinder; Mueller, Gernot H.; Lehnig, Manfred; Waldmann, Herbert Journal of Organic Chemistry, 2002 , vol. 67, # 20 p. 6902 - 6910

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Citation Number: 21

Abstract

The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14. 18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo-and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive ...