Development of new methodology for preparation of unusual amino acids as potential serine enzyme inhibitors

Since penicillin was discovered in the 1940's, many kinds of antibacterial drugs have been studied, and beta-lactam antibiotics including penicillin, which have lactam-ring, are the most widely used family of antibiotics for the control and treatment of bacterial infections. However, as the antibacterial drugs were more widely used, bacterial resistance evolved too. Therefore, it is crucial to keep developing novel antibacterial drugs. beta-lactams that have dithiodimethyl or disulfoxydimethyl groups at the C-4 position, different groups at the C-3 position and the N-1 position have been found to be good and useful compounds for this purpose. In this project, compounds that have an opened lactam-ring have been synthesized to further this goal. Opening the lactam-ring of the aforementioned beta-lactams results in 1,3-dicarbonyl compounds which can then be used for the addition of novel functional groups, providing new compounds for antibacterial action. The lactam-ring is opened by utilizing cerium(IV) ammonium nitrate, CAN.