By L. Bryan (Eds.)
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Additional resources for Antimicrobial Drug Resistance
Antimicrob. Agents Chemother. 17, 302. Zimmermann, W . , and Rosselet, A . (1977). Antimicrob. Agents Chemother. 12, 368. CHAPTER 2 ß-Lactams Resistant to Hydrolysis by the ß-Lactamases Jed Fisher Department of University of Minneapolis, Chemistry Minnesota Minnesota I. Introductory Remarks A. Perspectives B. Aspirations II. ß-Lactams as Acylating Reagents A. Intrinsic Reactivity B. Geometric Requirements for Membrane Peptidase Acylation . . III. ß-Lactams Resistant to the ß-Lactamases Α. ß-Lactams That Resist Acylation B.
1982). This mechanism is similar to that of acyclic amides having nitrogen leaving groups of comparable basicity, but different from that of monocyclic ß-lactams (rate-determining tetrahedral formation). The explanation offered by Proctor et al. for the increased alkaline reactivity of 2 5 bicyclic ß-lactams (~10 relative to monocyclic ß-lactams and ~ 1 0 relative to acyclic amides) is a higher steady-state concentration of the tetrahedral adduct, reflecting an added preference for a tetrahedral rather than trigonal carbon.
LACTAMS AS ACYLATING REAGENTS A . Intrinsic Reactivity A beneficial consequence of the immense variety of new ß-lactam structures now available is that the intrinsic features of these ß-lactams may be correlated with their biological activity, and trends discerned. Indeed, at one point it was anticipated that an understanding of intrinsic ß-lactam reactivity would be tantamount to understanding and predicting the basis for antibiotic activity. Although the rash optimism of this notion is now clear, the intrinsic reactivity of the ß-lactams remains the natural starting point in any discussion of the structural basis for ß-lactam antibiotic activity.
Antimicrobial Drug Resistance by L. Bryan (Eds.)