Diese praxisbezogene Reihe in 5 Bänden stützt sich auf Wissen und Erfahrungen der weltweit bedeutendsten Aminosäure-Forscher. Mit ihrer ausführlichen Diskussion von Vorkommen, Nutzen und Anwendungsbeispielen von Aminosäuren und ihren Polymeren (Peptiden und Proteinen) schließt sie eine Lücke in der Literatur.

InhaltsangabePART 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 RADICALMEDIATED SYNTHESIS OF ALPHAAMINO 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 SOLUTIONPHASE PEPTIDE SYNTHESIS Principle of Peptide Synthesis Protection Procedures Chain Elongation Procedures Final Deprotection Methods SOLIDPHASE 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 SolidPhase Organic Chemistry Early Applications of SPPS to Small Proteins SideReactions and SequenceDependent 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 SideReactions in Fmoc/tBu SolidPhase Peptide Synthesis Fmoc METHODOLOGY: CLEAVAGE FROM THE RESIN AND FINAL DEPROTECTION Introduction "Low" TFALabile Resins "High" TFALabile 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 SolidPhase 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 SideChainModified Peptides Cyclic Peptides LargeScale SolidPhase Synthesis Conclusions PEPTIDECOUPLING 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 PROT

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< ...