Nγ-Alkyl Derivatives of L-Glutamine as Inhibitors of Glutamine-Utilizing Enzymes

Abstract

A general, facile method to synthesize the Nγ-alkyl and Nγ,Nγ-dialkyl derivatives of L-glutamine 1a--d from L-glutamic acid as a starting substrate is presented. The obtained compounds are shown to inhibit three different glutamine-utilizing enzymes, namely: glutami-nase, γ-glutamyl transpeptidase, and glucosamine-6-phosphate synthase, with inhibitory constants within the millimolar range. © 2009, Verlag der Zeitschrift für Naturforschung. All rights reserved.