New Synthetic routes towards constrained cyclic peptides inspired by vancomycin

Abstract

Vancomycin is the last resort antibiotic against MRSA. Vancomycin causes the bacteria to die by physically blocking a recognition site within the cell wall. This recognition site binds to the inner cavity of vancomycin, which consists of a rigid bicyclic structure. The objective of my research was to mimic this bicyclic structure using synthetic alkene and alkyne bridges, and to see if a similar cavity was obtained. The alkene bridges were introduced using a (tandem) ring-closing metathesis reaction and the alkyne bridges were introduced by a Sonogashira reaction.