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The Chemistry of β-Lactams

It is over sixty years since Alexander Fleming observed antibiosis between a Penicillium mould and bacterial cultures and gave the name penicillin to the active principle. Although it was proposed in 1943 that penicillin (1) contained a tJ-Iactam ring, this was not generally accepted until an X-ray...

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Bibliographic Details
Other Authors: Page, M.I. (Editor)
Format: eBook
Language:English
Published: Dordrecht Springer Netherlands 1992, 1992
Edition:1st ed. 1992
Subjects:
Chemistry, Organic
Biochemistry
Organic Chemistry
Online Access:
Collection: Springer Book Archives -2004 - Collection details see MPG.ReNa
Table of Contents:
  • 9.5 Imidazolidinones
  • 9.6 Oxaziridines and epoxides
  • 9.7 Cydobutanones
  • 9.8 ?-Lactones
  • 9.9 Summary
  • References
  • 10 Classical ?-lactam structures
  • 10.1 Introduction
  • 10.2 Sheehan’s synthesis of penicillin V
  • 10.3 Woodward’s synthesis of cephalosporin C
  • 10.4 Biomimetic synthesis
  • 10.5 Merck synthesis of ( ± )-cephalothin
  • 10.6 The Hoechst synthesis
  • 10.7 Woodward’s penem synthesis
  • 10.8 The conversion of penicillins into cephalosporins
  • 10.9 Cephamycin antibiotics
  • 10.10 Merck synthesis of ( ± )-cefoxitin
  • 10.11 Shionogi synthesis of a 7-?-methoxy-1-oxacephem
  • 10.12 1 ,1-Dioxo-trans-7-methoxycephalosporanic acid t-butyl ester
  • References
  • Further reading
  • 1 The biosynthesis of ?-lactams
  • 1.1 Introduction
  • 1. 2 Penicillin and cephalosporin biosynthesis
  • 1.3 Clavulanic acid biosynthesis
  • 1.4 Carbapenem biosynthesis
  • 1.5 Monocyclic ?-lactam biosynthesis
  • References
  • 2 Structure-activity relationships: chemical
  • 2.1 The reactivity of the ?-lactam
  • 2.2 Structural and ground-state effects
  • 2.3 Kinetie effects
  • 2.4 Summary of kinetic and ground-state effects
  • 2.5 Structure-chemical reactivity relationships
  • 2.6 Ease of C-N bond fission in ?-lactams
  • References
  • 3 Structure-activity relationships: biological
  • 3.1 Introduction
  • 3.2 General aspects
  • 3.3 Natural penicillins
  • 3.4 Penicillinase-resistant antistaphylococcal penicillins
  • 3.5 Amino penicillins
  • 3.6 Carboxy and sulfo penicillins
  • 3.7 Acyl-ureido penicillins
  • 3.8 Amidino penicillanic acid penicillins
  • 3.9 6-?-Substituted penicillins
  • 3.10 Cephalosporins
  • 3.11 7-?-Acylamino group modifications
  • Acknowledgements
  • Dedication
  • References
  • 6 ?-Lactamase: mechanism of action
  • 6.1 Introduction
  • 6.2 Acyl-enzyme mechanism of ?-lactamase action: dass A ?-lactamases
  • 6.3 The acyl-enzyme mechanism of ?-lactamase action: class C ?-lactamases
  • 6.4 Metalloenzyme mechanism of ?-lactamase action
  • Acknowledgements
  • References
  • 7 ?-Lactamase: inhibition
  • 7.1 Introduction
  • 7.2 ?-Lactamase and DD-peptidase active sites: structure and mechanism
  • 7.3 Inhibitors of the serine ?-lactamase
  • 7.4 Inhibitors of class B (metallo) ?-lactamases
  • 7.5 Clinical indications
  • 7.6 Retrospects and prospects
  • References
  • 8 Novel ?-lactam structures - the carbacephems
  • 8.1 Introduction
  • 8.2 Nomenclature
  • 8.3 Synthesis
  • 8.4 Stability of the carbacephs
  • 8.5 Structure-activity relationships in the carbacephems
  • Acknowledgements
  • References
  • 9 Non-?-lactam mimics of ?-lactam antibiotics
  • 9.1 Introduction
  • 9.2 Pyrazolidinones
  • 9.3 Lactivicin
  • 9.4 ?-Lactams
  • 3.12 Substitutions on the 7-?-position
  • 3.13 C-3 Substituent modifications
  • 3.14 Orally adsorbed cephalosporins
  • 3.15 Oxacephalosporins
  • 3.16 Carbapenems
  • 3.17 Penems
  • 3.18 Monobactams
  • 3.19 ?-Lactamase inhibitors
  • 3.20 Conclusions
  • References
  • 4 The mechanisms of reactions of ?-lactams
  • 4.1 Introduction
  • 4.2 The aminolysis of ?-lactam antibiotics
  • 4.3 Metal-ion catalysed hydrolysis
  • 4.4 Micelle catalysed hydrolysis
  • 4.5 The direction of nucleophilic attack
  • 4.6 Thiazolidine ring opening
  • References
  • 5 Mode of action: interaction with the penicillin binding proteins
  • 5.1 Introduction
  • 5.2 Structure and biosynthesis of peptidoglycan
  • 5.3 Penicillin-recognizing proteins as members of an ‘active serine’ enzyme family
  • 5.4 Kinetics of the ?-lactam-PRP interaction
  • 5.5 The physiological function of PBPs
  • 5.6 PBPs involvedin resistance to ?-lactams
  • 5.7 Site-directed mutagenesis results
  • 5.8 Conclusions and perspectives

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