Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.
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.
Testero
Sebastian A
SA
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
O'Daniel
Peter I
PI
Shi
Qicun
Q
Lee
Mijoon
M
Hesek
Dusan
D
Ishiwata
Akihiro
A
Noll
Bruce C
BC
Mobashery
Shahriar
S
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*
C544039:6alpha-(1R-hydroxyoctyl)penicillanic acid; C544040:benzhydryl 6,6-dibromopenicillanate; D010397:Penicillanic Acid; D001618:beta-Lactamases