Enzymatic polymerization to an alternating N-l-cysteinyl chitin derivative: a novel class of multivalent glycopeptidomimetics

Abstract

A novel chitin derivative with an alternating N-l-cysteinyl group was successfully prepared. The precursor chitin derivative with an alternating N-l-thioprolinyl group could be obtained via chitinase-catalyzed polymerization of the N′-l-thioprolinyl chitobiose oxazoline derivative as a transition state analog substrate monomer under weak alkaline conditions. Conversion of the l-thioprolinyl group to an l-cysteinyl group in the product chitin derivative proceeded in a dose-dependent manner by methoxyamine hydrochloride, and the reaction could be completed almost quantitatively. The obtained chitin derivative is a uniformly amino acid-branching polysaccharide, which is categorized into a novel class of multivalent glycopeptidomimetics.