Asymmetric synthesis of an AmpC analog boronic acid

Abstract

The aim of this thesis is to synthetize a boronic acid analog of ampicillin. Ampicillin is a widely emloyed antibiotic in clinical use (for instance, the widely prescribed Augmentin from GlaxoSmithKline) but its use is limited by growing inactivation by β-lactamases, it is desirable necessary to design and synthetise molecules replacing them. Boronic acid bearing structure of ampicillin is likely to be a good ß-lactamase inhibitor. The closer the boronic acid resembles the natural substrate in its interactions with the enzyme, the better its inhibition.