The Chemistry and Biology of Beta-Lactams

Description

This new volume provides the most updated information about beta-lactams relating to both the pharmaceutical industry and synthetic chemistry. It provides the antibiotic activities as well as chemical reactivities of beta-lactams, which are important because they are commonly applied as antibiotics in the treatment of bacterial infections. The volume provides comprehensive coverage of most of the known beta-lactam antibiotics with both structural and biological information, antibiotic mechanisms, self-defense mechanisms of bacteria, nearly all known synthetic methods for the preparation of beta-lactams, and possible reactions in which beta-lactams can participate. Key features: Provides the most comprehensive collection of beta-lactam antibiotics (up to 269 molecules) with chemical structures, CAS number, IUPAC names and associated biological activities attached. Offers a comprehensive and detailed collection of beta-lactamase databases. Explains the self-defense mechanisms of bacteria for surviving, including the formation of biofilm and conversion into L-form and secretion of beta-lactamase to deactivate the beta-lactam antibiotics. Provides a comprehensive survey on the synthetic methods to make beta-lactams. Gives all of the possible reactions involving beta-lactams as the starting materials. Surveys over 1000 research works and includes all available DOI information. The volume is a valuable resource on the antibiotic activities as well as chemical reactivities of beta-lactams for researchers and scientists, faculty, and advanced students, as well as for industry professionals working in medicinal and pharmaceutical chemistry, organic chemistry, organic synthesis, heterocycles, proteins and peptides. Cover Half Title The Chemistry and Biology of Beta-Lactams Copyright About the Author Contents Abbreviations Acknowledgments Preface 1. β-Lactams and Antibiotics 1.1 Brief Introduction 1.2 Penicillin Antibiotics 1.3 Cephalosporin Antibiotics 1.4 Carbapenem Antibiotics 1.5 Monobactam Antibiotics 1.6 Clavam Antibiotics 1.7 Miscellaneous β-Lactam Antibiotics Keywords References 2. Antimicrobial Activity of β-Lactams and Bacterial Resistance 2.1 Brief Introduction of Bacteria 2.2 Nomenclature and Classification of Bacteria 2.3 Antibacterial Mechanism 2.4 Resistance of Antibacterial Activity 2.5 Mechanisms for Antibiotics Resistance 2.6 β-Lactamases Databases 2.6.1 Antibiotic Resistance Genes Database (ARDB) 2.6.2 Antibiotic Resistance Genes Online (ARGO) 2.6.3 Bacmet: Antibacterial Biocide and Metal Resistance Genes Database 2.6.4 Blad β-Lactams Database 2.6.5 Beta-Lactamase Database (BLDB) 2.6.6 Bacterial Antimicrobial Resistance Reference Gene Database (Bioproject Accession Number PRJNA313047) 2.6.7 The Comprehensive Antibiotic Resistance Database (CARD) 2.6.8 Comprehensive β-Lactamase Molecular Annotation Resource (CBMAR) 2.6.9 Comprehensive Online Database of β-Lactamase Enzymes (CODLE) 2.6.10 European Antimicrobial Resistance Surveillance Network (EARS-NET) 2.6.11 The Functional Antibiotic-Resistant Metagenomic Element (FARME) 2.6.12 Integrall 2.6.13 Interpro 2.6.14 Kyoto Encyclopedia of Genes and Genomes (KEGG) 2.6.15 Lactamase Engineering Database (LACED) 2.6.16 The Lahey Clinic Database 2.6.17 Megares: an Antimicrobial Database for High-throughput Sequencing 2.6.18 Mustard: Antibiotic Resistance Determinants (ARDS) Database 2.6.19 National Database of Antibiotic-Resistant Organisms (NDARO) 2.6.20 Pathosystems Resource Integration Center (PATRIC) 2.6.21 Repository of Antibiotic Resistance Cassettes (RAC) 2.7 Other Biological Activities of β-Lactams Keywords References 3. Synthetic Methods of β-Lactams 3.1 Brief Introduction 3.2 Formation of β-Lactams Through Cycloadditions 3.2.1 Staudinger’s [2+2] Cycloaddition 3.2.2 Wolff Rearrangement Pathway to β-Lactams 3.2.3 [2+2]-Cycloaddition Between Alkene and Isocyanate 3.2.4 Kinugasa Reaction 3.3 Intramolecular Substitutive Cyclization 3.3.1 Intramolecular Michael Addition and Electrocyclic Ring Closure 3.3.2 Photolysis of α,β-Unsaturated Amides 3.3.3 Intramolecular Cyclization with Nitrogenous Nucleophiles 3.3.4 Intramolecular Cyclization with Carbon Nucleophiles 3.3.5 Intramolecular Amide Formation 3.3.6 Formation of β-Lactams via Amidation 3.3.7 Syntheses of β-Lactams from Aziridines 3.3.8 Carbonylation of Allylamines 3.3.9 Ugi Multi-Component Reaction (MCR) 3.3.10 Ring Contractions 3.4 Enzymatic Synthesis of β-Lactams 3.5 Miscellaneous Methods Keywords References 4. Reactions of β-Lactams 4.1 Brief Introduction 4.2 Cleavage of the Amide Bond of β-Lactams 4.2.1 Hydrolysis of β-Lactams 4.2.2 Alcoholysis of β-Lactams 4.2.3 Aminolysis of β-Lactams 4.2.4 Hydrazinolysis of β-Lactams 4.2.5 Tholysis of β-Lactams 4.2.6 Cleavage of β-Lactams by Hydride 4.2.7 Miscellaneous Reaction Relating to the Cleavage of Amide Bonds 4.3 Preparation of Polyamides 4.4 Application in the Synthesis of Unnatural α-Amino Acid Derivatives and Relating Peptides 4.5 Nucleophilic Substitution on C3 or C4 4.6 Cleavage of C3-C4 Bond 4.7 Cleavage of N1-C4 Bond 4.8 Function at N1 Keywords References Index