title: Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.
abstract: The unique hydrophobic surface patches in class D beta-lactamases presented an opportunity for designing two compounds, 6alpha-(1R-hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid, as mechanistic probes of these enzymes. In a sequence of three synthetic steps from benzhydryl 6,6-dibromopenicillanate, the targeted compounds were prepared in a stereospecific manner.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Sebastian A
authors.initials: SA
authors.lastname: Testero
authors.forename: Peter I
authors.initials: PI
authors.lastname: O'Daniel
authors.forename: Qicun
authors.initials: Q
authors.lastname: Shi
authors.forename: Mijoon
authors.initials: M
authors.lastname: Lee
authors.forename: Dusan
authors.initials: D
authors.lastname: Hesek
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ishiwata
authors.forename: Bruce C
authors.initials: BC
authors.lastname: Noll
authors.forename: Shahriar
authors.initials: S
authors.lastname: Mobashery
mesh_terms: D018360:Crystallography, X-Ray; D057927:Hydrophobic and Hydrophilic Interactions; D008968:Molecular Conformation; D015394:Molecular Structure; D010397:Penicillanic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D001618:beta-Lactamases / Q000737:chemistry*
chemical_list: C544039:6alpha-(1R-hydroxyoctyl)penicillanic acid; C544040:benzhydryl 6,6-dibromopenicillanate; D010397:Penicillanic Acid; D001618:beta-Lactamases