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This is the third of five books in the Amino Acids, Peptides and Proteins in Organic Synthesis series. Closing a gap in the literature, this is the only series to cover this important topic in organic and biochemistry. Drawing upon the combined expertise of the international "who's who" in amino acid research, these volumes represent a real benchmark for amino acid chemistry, providing a comprehensive discussion of the occurrence, uses and applications of amino acids and, by extension, their polymeric forms, peptides and proteins. The practical value of each volume is heightened by the…mehr
This is the third of five books in the Amino Acids, Peptides and Proteins in Organic Synthesis series. Closing a gap in the literature, this is the only series to cover this important topic in organic and biochemistry. Drawing upon the combined expertise of the international "who's who" in amino acid research, these volumes represent a real benchmark for amino acid chemistry, providing a comprehensive discussion of the occurrence, uses and applications of amino acids and, by extension, their polymeric forms, peptides and proteins. The practical value of each volume is heightened by the inclusion of experimental procedures. This third volume in the series presents an in depth account of recent developments in the (bio-)synthesis of amino acids and peptides. Divided into two parts, the first section deals with amino acids as building blocks, including the generation of alpha-amino acids, beta-lactams, and heterocycles. The second section is devoted to the synthesis of peptides, with the focus on solid phase synthesis. However, solution phase peptide synthesis is covered as well, as are topics such as coupling reagents, chemical ligation, peptide purfication and automation.
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 Ley´s 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.
Inhaltsangabe
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 Prize Automation of SPPS Impact of New Protecting Groups and Resin Linkages Solid-Phase Organic Chemistry Early Applications of SPPS to Small Proteins Side-Reactions and Sequence-Dependent Problems Rapid Expansion of Usage Leading to the Nobel Prize From the Nobel Prize Forward to Combinatorial Chemistry Protein Synthesis and Peptide Ligation Conclusions LINKERS FOR SOLID-PHASE PEPTIDE SYNTHESIS Introduction Immobilization via Carboxyl Group Imobilization via Amino Group Backbone Immobilization Immobilization via Amino Acid Side-Chain Conclusions ORTHOGONAL PROTECTING GROUPS AND SIDE-REACTIONS IN Fmoc/tBu SOLID-PHASE PEPTIDE SYNTHESIS Orthogonal Protecting Groups in Fmoc/tBu Solid-Phase Peptide Synthesis Side-Reactions in Fmoc/tBu Solid-Phase Peptide Synthesis Fmoc METHODOLOGY: CLEAVAGE FROM THE RESIN AND FINAL DEPROTECTION Introduction "Low" TFA-Labile Resins "High" TFA-Labile Resins Final Remarks STRATEGY IN SOLID-PHASE PEPTIDE SYNTHESIS Synthetic Strategies Utilizing Solid-Phase Peptide Synthesis Methods Solid Support: Resins and Linkers Developing the Synthetic Strategy: Selection of the Protecting Group Scheme Resin Loading SBS Peptide Chain Elongation: Coupling and Activation Piperazine Formation Solid-Phase Synthesis of Protected Peptide Segments Fragment Condensation Approach: Convergent and Hybrid Synteses Cleavage from the Resin and Global Peptide Deprotection Disulfide Bond-Containing Peptides Native Chemical Ligation (NCL) SPPS of Peptides Modified at their C-Terminus Side-Chain-Modified Peptides Cyclic Peptides Large-Scale Solid-Phase Synthesis Conclusions PEPTIDE-COUPLING REAGENTS Introduction Carbodiimides Phosphonium Salts Aminium/Uronium Salts Fluoroformamidinium Coupling Reagents Organophosphorus Reagents Triazine Coupling Reagents Mukaiyama's Reagent Conclusions CHEMOSELECTIVE PEPTIDE LIGATION: A PRIVILEGED TOOL FOR PROTEIN SYNTHESIS Introduction Chemoselective Peptide Ligations Following a Capture/Rearrangement Strategy Chemical Transf
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 Prize Automation of SPPS Impact of New Protecting Groups and Resin Linkages Solid-Phase Organic Chemistry Early Applications of SPPS to Small Proteins Side-Reactions and Sequence-Dependent Problems Rapid Expansion of Usage Leading to the Nobel Prize From the Nobel Prize Forward to Combinatorial Chemistry Protein Synthesis and Peptide Ligation Conclusions LINKERS FOR SOLID-PHASE PEPTIDE SYNTHESIS Introduction Immobilization via Carboxyl Group Imobilization via Amino Group Backbone Immobilization Immobilization via Amino Acid Side-Chain Conclusions ORTHOGONAL PROTECTING GROUPS AND SIDE-REACTIONS IN Fmoc/tBu SOLID-PHASE PEPTIDE SYNTHESIS Orthogonal Protecting Groups in Fmoc/tBu Solid-Phase Peptide Synthesis Side-Reactions in Fmoc/tBu Solid-Phase Peptide Synthesis Fmoc METHODOLOGY: CLEAVAGE FROM THE RESIN AND FINAL DEPROTECTION Introduction "Low" TFA-Labile Resins "High" TFA-Labile Resins Final Remarks STRATEGY IN SOLID-PHASE PEPTIDE SYNTHESIS Synthetic Strategies Utilizing Solid-Phase Peptide Synthesis Methods Solid Support: Resins and Linkers Developing the Synthetic Strategy: Selection of the Protecting Group Scheme Resin Loading SBS Peptide Chain Elongation: Coupling and Activation Piperazine Formation Solid-Phase Synthesis of Protected Peptide Segments Fragment Condensation Approach: Convergent and Hybrid Synteses Cleavage from the Resin and Global Peptide Deprotection Disulfide Bond-Containing Peptides Native Chemical Ligation (NCL) SPPS of Peptides Modified at their C-Terminus Side-Chain-Modified Peptides Cyclic Peptides Large-Scale Solid-Phase Synthesis Conclusions PEPTIDE-COUPLING REAGENTS Introduction Carbodiimides Phosphonium Salts Aminium/Uronium Salts Fluoroformamidinium Coupling Reagents Organophosphorus Reagents Triazine Coupling Reagents Mukaiyama's Reagent Conclusions CHEMOSELECTIVE PEPTIDE LIGATION: A PRIVILEGED TOOL FOR PROTEIN SYNTHESIS Introduction Chemoselective Peptide Ligations Following a Capture/Rearrangement Strategy Chemical Transf
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