Synthesis of a modified carboxylate-binding pocket of vancomycin

A 16-membered tetrapeptide macrocycle I, an analog of the vancomycin binding pocket, has been designed and synthesized using the efficient macrocyclization of the corresponding linear tetrapeptide via biaryl ether formation. In acetone, I adopted a right conformation needed for binding carboxylate anion even in the absence of -Ac-D-Ala-D-Ala-OH. [on SciFinder (R)]