title: Synthesis and reactivity with beta-lactamases of a monobactam bearing a retro-amide side chain.
abstract: The monobactam sodium 3-benzylcarbamoyl-2-oxo-1-azetidinesulfonate, bearing a retro (vs classical beta-lactam)-amide side chain, has been synthesized and the kinetics of its reaction with typical beta-lactamases studied. The new compound is generally a poorer substrate than the analogous compound with a normal side chain but its formation of a transiently stable complex with a class C beta-lactamase sustains the retro-amide side-chain concept.
authors.affiliation: Department of Chemistry, Wesleyan University, Middletown, CT 06459, USA.
authors.forename: S A
authors.initials: SA
authors.lastname: Adediran
authors.forename: J-F
authors.initials: JF
authors.lastname: Lohier
authors.forename: D
authors.initials: D
authors.lastname: Cabaret
authors.forename: M
authors.initials: M
authors.lastname: Wakselman
authors.forename: R F
authors.initials: RF
authors.lastname: Pratt
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D016972:Enterobacter cloacae / Q000201:enzymology; D006868:Hydrolysis; D007700:Kinetics; D008968:Molecular Conformation; D008997:Monobactams / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D001618:beta-Lactamases / Q000737:chemistry*
chemical_list: D000577:Amides; D008997:Monobactams; D001618:beta-Lactamases