New alpha, beta-epoxysulfonic acid derivatives 2, 17 and 18, topologically related to monobactams, have been prepared by epoxidation of alpha, beta-unsaturated sulfonates. These were readily obtained from (2R)-N-acylalaninals 7 or protected (syn)-3-hydroxy-2-methylbutanal 24 (+/-) and phosphonate reagents 11 or 12. Compounds 2 and 18 showed no biological activity but the betaine 15 showed a weak anti-beta-lactamase activity.
Carretero, J. C., Davies, J., Marchand-Brynaert, J., & Ghosez, L. (1990). Synthesis of Alpha, Beta-epoxysulfonic Acids As Potential Inhibitors of Bacterial D,D-peptidases. Societe Chimique de France. Bulletin, 6, 835-842. https://hdl.handle.net/2078.5/137930 (Original work published 1990)