Amino Acids, Peptides and Proteins in Organic Chemistry / Amino Acids, Peptides and Proteins in Organic Chemistry Bd.3 (ePub)

PART I: Amino Acids as Building Blocks AMINO ACID BIOSYNTHESIS Introduction Glutamate and Glutamine: Gateways to Amino Acid Bioynthesis Other Amino Acids from Ubiquitous Metabolites: Pyridoxal Phosphate-Dependent Routes to Aspartate, Alanine, and Glycine Routes to Functionalized Three-Carbon Amino Acids: Serine, Cysteine, and Selenocysteine Other Amino Acids fron Aspartate and Glutamate: Asparagine and Side Chain Functional Group Manipulation Aspartate and Glutamate Families of Amino Acids Biosynthesis of Aliphatic Amino Acids with Modified Carbon Skeletons: Branched-Chain Amino Acids, Lysine, and Pyrrolysine Biosynthesis of the Aromatic Amino Acids Conclusions HETEROCYCLES FROM AMINO ACIDS Introduction Heterocycles Generated by Intramolecular Cyclizations Heterocycles Generated by Intermolecular Cyclizations Heterocycles Generated by Cycloadditions Conclusions Experimental Procedures RADICAL-MEDIATED SYNTHESIS OF ALPHA-AMINO ACIDS AND PEPTIDES Introduction Free Radical Reactions Radical Addition to Imine Derivatives Radical Conjugate Addition Conclusions Experimental Protocols SYNTHESIS OF BETA-LACTAMS (CEPHALOSPORINS) BY BIOCONVERSION Introduction Biosynthetic Pathways of Cephalosporins and Penicillins Production of 7-ACA by A. chrysogenum Production of 7-ADCA by A. chrysogenum Production of Penicillin G by A. chrysogenum Production of Cephalosporins by P. chrysogenum Conversion of Penicillin G and other Penicillins to DAOG by Streptomyces clavuligerus Conclusions STRUCTURE AND REACTIVITY OF BETA-LACTAMS Introduction Structure Reactivity Hydrolysis Aminolysis Epimerization PART II: Amino Acid Coupling Chemistry SOLUTION-PHASE PEPTIDE SYNTHESIS Principle of Peptide Synthesis Protection Procedures Chain Elongation Procedures Final Deprotection Methods SOLID-PHASE PEPTIDE SYNTHESIS: HISTORICAL ASPECTS Introduction Selection of Compatible Synthetic Components Racemization and Stepwise Peptide Assembly Optimization of Synthetic Components Foreshadowing of the Nobel

Andrew Hughes is a reader and Head of the Department of Chemistry, La Trobe University, Melbourne, Australia. He obtained his degrees from the University of Western Australia before taking up post-doctoral appointments at the University of Cambridge starting 1989. After three years working with Professor Andrew Holmes, he joined Professor Steven Leys group. While at Cambridge he was appointed the Shell Research Fellow at Robinson College. His interests lie in the general field of asymmetric synthesis and methodology, with a recent focus on amino acid chemistry.

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