The Chemistry and Biology of Beta-Lactams PDF
Preview The Chemistry and Biology of Beta-Lactams
THE CHEMISTRY AND BIOLOGY OF BETA-LACTAMS THE CHEMISTRY AND BIOLOGY OF BETA-LACTAMS Zerong Wang, PhD First edition published 2023 Apple Academic Press Inc. CRC Press 1265 Goldenrod Circle, NE, 6000 Broken Sound Parkway NW, Palm Bay, FL 32905 USA Suite 300, Boca Raton, FL 33487-2742 USA 760 Laurentian Drive, Unit 19, 4 Park Square, Milton Park, Burlington, ON L7N 0A4, CANADA Abingdon, Oxon, OX14 4RN UK © 2023 by Apple Academic Press, Inc. Apple Academic Press exclusively co-publishes with CRC Press, an imprint of Taylor & Francis Group, LLC Reasonable efforts have been made to publish reliable data and information, but the authors, editors, and publisher cannot assume responsibility for the validity of all materials or the consequences of their use. The authors, editors, and publishers have attempted to trace the copyright holders of all material reproduced in this publication and apologize to copyright holders if permission to publish in this form has not been obtained. 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Library and Archives Canada Cataloguing in Publication Title: The chemistry and biology of Beta-Lactams / Zerong Wang, PhD. Names: Wang, Zerong (Daniel Zerong), author. Description: First edition. | Includes bibliographical references and index. Identifiers: Canadiana (print) 20220443939 | Canadiana (ebook) 20220443971 | ISBN 9781774911716 (hardcover) | ISBN 9781774911723 (softcover) | ISBN 9781003330288 (ebook) Subjects: LCSH: Beta lactamases. Classification: LCC QP609.B46 W36 2023 | DDC 579.3/5—dc23 Library of Congress Cataloging-in-Publication Data CIP data on file with US Library of C ongress ISBN: 978-1-77491-171-6 (hbk) ISBN: 978-1-77491-172-3 (pbk) ISBN: 978-1-00333-028-8 (ebk) About the Author Zerong Wang, PhD Professor of Chemistry, College of Science and Engineering, University of Houston-Clear Lake, Texas, USA Zerong Wang, PhD, is a Full Professor at the University of Houston-Clear Lake, Texas. Prior to that, he worked at the Institute for Biological Sciences of the National Research Council of Canada for several years. Through his career, the author has gained specific training and expertise in organic chem- istry, particularly in physical and organic chemistry and other subdisciplines that include photochemistry, spectroscopies, carbohydrate chemistry, sulfur chemistry, nucleosides and heterocycles, material science, reaction meth- odology, computational chemistry, among other. Dr. Wang has developed research projects relating to sulfur chemistry, computational chemistry, nucleoside analogs, heterocycle chemistry, materials science, and macro- molecules (pillarene, calix[n]arene, and melamine-based dendrimers, etc.) and has received 22 research grants, including from NSF-MRI, NSF-STEM, Welch Research Grant, Welch Departmental Research Grant, and University of Houston-Clear Lake’s Faculty Research and Support Fund (FRSF) Grants. The author has developed two compendiums in organic chemistry: Comprehensive Organic Named Reactions, with Detailed Mechanism Discussions and Updated Experimental Procedures (3 volumes) (Wiley, 2009) and Encyclopedia of Physical Organic Chemistry (6 volumes) (Wiley, 2017), the PROSE Award winner in 2018. While conducting research activities, the author also teaches courses for both graduate and undergraduate students. To date, the author has taught courses on General Chemistry, General Chemistry Laboratory, Analytical Chemistry, Quantitative Chemical Analysis, Forensic Chemistry, Organic Chemistry, Organic Chemistry Laboratory, Advanced Organic Chemistry, Physical Organic Chemistry, Synthetic Organic Chemistry, Organometallic Chemistry, Biochemistry, Biochemistry Laboratory, Polymer Chemistry, Introduction to Chemical Engineering, Nutrition and Diet Chemistry, Green Chemistry, Introduction to NMR Spectroscopy, Chemistry Seminar, Graduate Research, and Chemistry for Non-Science Majors. vi About the Author Dr. Wang earned his BS degree in Chemistry from Lanzhou University, PR China, and earned his MS and PhD degrees from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences. He conducted his postdoctoral research at the Department of Chemistry, University of Cali- fornia Berkeley and York University (Canada). Contents Abbreviations ...........................................................................................................ix Acknowledgments ...................................................................................................xiii Preface ....................................................................................................................xv 1. β-Lactams and Antibiotics ..............................................................................1 1.1 Brief Introduction ............................................................................................................1 1.2 Penicillin Antibiotics .......................................................................................................3 1.3 Cephalosporin Antibiotics .............................................................................................13 1.4 Carbapenem Antibiotics ................................................................................................14 1.5 Monobactam Antibiotics ...............................................................................................33 1.6 Clavam Antibiotics ........................................................................................................61 1.7 Miscellaneous β-Lactam Antibiotics .............................................................................63 Keywords ...............................................................................................................................73 References .............................................................................................................................74 2. Antimicrobial Activity of β-Lactams and Bacterial Resistance .................91 2.1 Brief Introduction of Bacteria .......................................................................................91 2.2 Nomenclature and Classification of Bacteria ................................................................93 2.3 Antibacterial Mechanism ..............................................................................................94 2.4 Resistance of Antibacterial Activity ............................................................................100 2.5 Mechanisms for Antibiotics Resistance ......................................................................101 2.6 β-Lactamases Databases .............................................................................................109 2.7 Other Biological Activities of β-Lactams ...................................................................120 Keywords .............................................................................................................................130 References ...........................................................................................................................130 3. Synthetic Methods of β-Lactams ................................................................139 3.1 Brief Introduction ........................................................................................................139 3.2 Formation of β-Lactams Through Cycloadditions ......................................................139 3.3 Intramolecular Substitutive Cyclization......................................................................204 3.4 Enzymatic Synthesis of β-Lactams .............................................................................300 3.5 Miscellaneous Methods...............................................................................................303 Keywords .............................................................................................................................321 References ...........................................................................................................................321 viii Contents 4. Reactions of β-Lactams ...............................................................................357 4.1 Brief Introduction ........................................................................................................357 4.2 Cleavage of the Amide Bond of β-Lactams ................................................................358 4.3 Preparation of Polyamides ..........................................................................................390 4.4 Application in the Synthesis of Unnatural α-Amino Acid Derivatives and Relating Peptides ........................................................................................................399 4.5 Nucleophilic Substitution on C3 or C4 .......................................................................408 4.6 Cleavage of C3-C4 Bond ............................................................................................409 4.7 Cleavage of N1-C4 Bond ............................................................................................411 4.8 Function at N1 .............................................................................................................416 Keywords .............................................................................................................................419 References ...........................................................................................................................419 Index .....................................................................................................................431 Abbreviations ACE angiotensin-converting enzyme ADAC acyclic diaminocarbenes AMR access antimicrobial resistance APAF-1 apoptotic protease activating factor 1 ARDB antibiotic resistance genes database ARDs antibiotic resistance determinants ARGO antibiotic resistance genes online ARO antibiotic resistance ontology BHT butylated hydroxytoluene BLAD beta-lactamase database BLAST basic local alignment search tool BLDB beta-lactamase database BTPP tert-butylimino-tri(pyrrolidino)phosphorane CAACs cyclic (alkyl)(amino)carbenes CAL-B Candida Antarctica lipase B CAN ceric ammonium nitrate CARD comprehensive antibiotic resistance database CBMAR comprehensive β-lactamase molecular annotation resource CDC centers for disease control and prevention CDD conserved domains database CMPI 2-chloro-1-methylpyridinium iodide CODLE comprehensive online database of β-lactamase enzymes COG clusters of orthologous groups of proteins CSI chlorosulfonyl isocyanate DABCO 1,4-diazabicyclo[2.2.2]octane DEAD diethyl azodicarboxylate DIAD diisopropyl azodicarboxylate DIPEA diisopropylethylamine DMDO dimethyldioxirane DME 1,2-dimethoxyethane DMPU N,N’-dimethylpropyleneurea EARS-Net European Antimicrobial Resistance Surveillance Network ECDC European Center for Disease Prevention and Control EDCI 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide x Abbreviations EDTA ethylenediaminetetraacetic acid ESBL extended-spectrum beta-lactamases FARME functional antibiotic resistant metagenomic element FDA Food and Drug Administration GES Guiana-extended-spectrum HCMV human cytomegalovirus HIV-1 PR human immunodeficiency virus type 1 proteinase HMMs hidden Markov models HWE Horner-Wadsworth-Emmons IBC-Cl isobutyl carbonochloridate IJSB international journal of systematic bacteriology IJSEM International Journal of Systematic and Evolutionary Microbiology IMDs indwelling medical devices IMP imipenemase KEGG Kyoto Encyclopedia of Genes and Genomes KOTMS potassium trimethylsilanolate KPC Kiebsiella pneumoniae carbapenemase LacED lactamase engineering database LDL low-density lipoproteins MBLs metallo-β-lactamases MCR multi-component reaction MDR multi-drug resistant MIC minimal inhibitory concentration MRIs mobile resistance integrons MRSA methicillin-resistant staphylococcus aureus NAAA N-acylethanolamine acid amidase NCA N-carboxyanhydride NCBI National Center for Biotechnology Information NCS N-chlorosuccinimide NDARO national database of antibiotic-resistant organisms NDM New Delhi MBL NHC N-heterocyclic carbene NMI N-methylimidazole OBHA·HCl O-benzylhydroxylamine hydrochloride PASs poly(amido-saccharide)s PATRIC pathosystems resource integration center PBPs penicillin-binding proteins PBS phosphate-buffered saline
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