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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Crystallography, X-Ray
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Hydrophobic and Hydrophilic Interactions
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Molecular Conformation
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Molecular Structure
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Penicillanic Acid / analogs & derivatives*
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Penicillanic Acid / chemical synthesis
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Penicillanic Acid / chemistry
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Stereoisomerism
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beta-Lactamases / chemistry*
Substances
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6alpha-(1R-hydroxyoctyl)penicillanic acid
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benzhydryl 6,6-dibromopenicillanate
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Penicillanic Acid
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beta-Lactamases