The Synthesis and Structure of a Cyclobutane Analog of Glutamic Acid With an Acetic Acid Side Chain

Abstract

A synthetic route involving a hydantoin derivative of bicyclo [3.2.0]hept-2-ene has been investigated for the preparation of neurotransmitter analogues containing an additional acetic acid substituent on the cyclobutane ring of the potent NMDA receptor agonist trans-1-aminocyclobutane-1,3-dicarboxylic acid. X-Ray analysis showed that the major cyclobutane amino acid produced had the 2-acetic acid and 3-carboxylic acid substituents in the trans orientation as a result of epimerization during hydantoin hydrolysis.