Published in
American Chemical Society, Organic Letters, 12(11), p. 2515-2518, 2009
DOI: 10.1021/ol900668k
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Regiospecific Syntheses of 6α-(1R-hydroxyoctyl)penicillanic acid and 6β-(1R-hydroxyoctyl)penicillanic acid as Mechanistic Probes of Class D β-Lactamases
Journal article published in 2009 by
Sebastian A. Testero,
Peter I. O’Daniel,
Qicun Shi,
Mijoon Lee,
Dusan Hesek,
Akihiro Ishiwata 
,
Bruce C. Noll,
Shahriar Mobashery
,
Bruce C. Noll,
Shahriar Mobashery
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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.