Synthesis of A Modified Carboxylate-binding Pocket of Vancomycin

Abstract

A 16-membered tetrapeptidic macrocycle (4), analog of vancomycin binding pocket, has been designed and synthesized using the efficient macrocyclisation of the corresponding linear tetrapeptide (14) via biaryl ether formation. In aceton, compound 4 adopted a right conformation needed for binding carboxylate anion even in the absence of N-Ac-D-Ala-D-Ala.