Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.
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ABSTRACT:
SUBMITTER: Testero SA
PROVIDER: S-EPMC3297418 | biostudies-literature | 2009 Jun
REPOSITORIES: biostudies-literature
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Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.
Testero Sebastian A SA O'Daniel Peter I PI Shi Qicun Q Lee Mijoon M Hesek Dusan D Ishiwata Akihiro A Noll Bruce C BC Mobashery Shahriar S
Organic letters 20090601 12
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. ...[more]
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