Building Blocks, Catalysis and Coupling Chemistry
(Sprache: Englisch)
Closing a gap in the literature, this practical book series in 5 volumes draws on the expertise of the "who s who" in amino acid research to provide a comprehensive discussion of the occurrence, uses and applications of amino acids, their polymeric forms, peptides and proteins.
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Produktinformationen zu „Building Blocks, Catalysis and Coupling Chemistry “
Closing a gap in the literature, this practical book series in 5 volumes draws on the expertise of the "who s who" in amino acid research to provide a comprehensive discussion of the occurrence, uses and applications of amino acids, their polymeric forms, peptides and proteins.
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Klappentext zu „Building Blocks, Catalysis and Coupling Chemistry “
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.
Inhaltsverzeichnis zu „Building Blocks, Catalysis and Coupling Chemistry “
PART I: Amino Acids as Building BlocksAMINO ACID BIOSYNTHESISIntroductionGlutamate and Glutamine: Gateways to Amino Acid BioynthesisOther Amino Acids from Ubiquitous Metabolites: Pyridoxal Phosphate-Dependent Routes to Aspartate, Alanine, and GlycineRoutes to Functionalized Three-Carbon Amino Acids: Serine, Cysteine, and SelenocysteineOther Amino Acids fron Aspartate and Glutamate: Asparagine and Side Chain Functional Group ManipulationAspartate and Glutamate Families of Amino AcidsBiosynthesis of Aliphatic Amino Acids with Modified Carbon Skeletons: Branched-Chain Amino Acids, Lysine, and PyrrolysineBiosynthesis of the Aromatic Amino AcidsConclusionsHETEROCYCLES FROM AMINO ACIDSIntroductionHeterocycles Generated by Intramolecular CyclizationsHeterocycles Generated by Intermolecular CyclizationsHeterocycles Generated by CycloadditionsConclusionsExperimental ProceduresRADICAL-MEDIATED SYNTHESIS OF ALPHA-AMINO ACIDS AND PEPTIDESIntroductionFree Radical ReactionsRadical Addition to Imine DerivativesRadical Conjugate AdditionConclusionsExperimental ProtocolsSYNTHESIS OF BETA-LACTAMS (CEPHALOSPORINS) BY BIOCONVERSIONIntroductionBiosynthetic Pathways of Cephalosporins and PenicillinsProduction of 7-ACA by A. chrysogenumProduction of 7-ADCA by A. chrysogenumProduction of Penicillin G by A. chrysogenumProduction of Cephalosporins by P. chrysogenumConversion of Penicillin G and other Penicillins to DAOG by Streptomyces clavuligerusConclusionsSTRUCTURE AND REACTIVITY OF BETA-LACTAMSIntroductionStructureReactivityHydrolysisAminolysisEpimerizationPART II: Amino Acid Coupling ChemistrySOLUTION-PHASE PEPTIDE SYNTHESISPrinciple of Peptide SynthesisProtection ProceduresChain Elongation ProceduresFinal Deprotection MethodsSOLID-PHASE PEPTIDE SYNTHESIS: HISTORICAL ASPECTSIntroductionSelection of Compatible Synthetic ComponentsRacemization and Stepwise Peptide AssemblyOptimization of Synthetic ComponentsForeshadowing of the Nobel PrizeAutomation of SPPSImpact of New Protecting Groups
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and Resin LinkagesSolid-Phase Organic ChemistryEarly Applications of SPPS to Small ProteinsSide-Reactions and Sequence-Dependent ProblemsRapid Expansion of Usage Leading to the Nobel PrizeFrom the Nobel Prize Forward to Combinatorial ChemistryProtein Synthesis and Peptide LigationConclusionsLINKERS FOR SOLID-PHASE PEPTIDE SYNTHESISIntroductionImmobilization via Carboxyl GroupImobilization via Amino GroupBackbone ImmobilizationImmobilization via Amino Acid Side-ChainConclusionsORTHOGONAL PROTECTING GROUPS AND SIDE-REACTIONS IN Fmoc/tBu SOLID-PHASE PEPTIDE SYNTHESISOrthogonal Protecting Groups in Fmoc/tBu Solid-Phase Peptide SynthesisSide-Reactions in Fmoc/tBu Solid-Phase Peptide SynthesisFmoc METHODOLOGY: CLEAVAGE FROM THE RESIN AND FINAL DEPROTECTIONIntroduction"Low" TFA-Labile Resins"High" TFA-Labile ResinsFinal RemarksSTRATEGY IN SOLID-PHASE PEPTIDE SYNTHESISSynthetic Strategies Utilizing Solid-Phase Peptide Synthesis MethodsSolid Support: Resins and LinkersDeveloping the Synthetic Strategy: Selection of the Protecting Group SchemeResin LoadingSBS Peptide Chain Elongation: Coupling and ActivationPiperazine FormationSolid-Phase Synthesis of Protected Peptide SegmentsFragment Condensation Approach: Convergent and Hybrid SyntesesCleavage from the Resin and Global Peptide DeprotectionDisulfide Bond-Containing PeptidesNative Chemical Ligation (NCL)SPPS of Peptides Modified at their C-TerminusSide-Chain-Modified PeptidesCyclic PeptidesLarge-Scale Solid-Phase SynthesisConclusionsPEPTIDE-COUPLING REAGENTSIntroductionCarbodiimidesPhosphonium SaltsAminium/Uronium SaltsFluoroformamidinium Coupling ReagentsOrganophosphorus ReagentsTriazine Coupling ReagentsMukaiyama's ReagentConclusionsCHEMOSELECTIVE PEPTIDE LIGATION: A PRIVILEGED TOOL FOR PROTEIN SYNTHESISIntroductionChemoselective Peptide Ligations Following a Capture/Rearrangement StrategyChemical Transformations for Cys-Free Ligations in Peptides and ProteinsOther Chemoselective Capture StrategiesPeptide Ligations by Chemoselective Amide-Bond-Forming ReactionsStrategies for the Ligation of Multiple FragmentsAUTOMATION OF PEPTIDE SYNTHESISIntroductionSPPS: From Mechanization to AutomationDeprotection Step: Monitoring and ControlCoupling Step: Monitoring and ControlIntegrated Deprotection and Coupling ControlPEPTIDE PURIFICATION BY REVERSED-PHASE CHROMATOGRAPHYRP-HPLC of PeptidesPeptide PropertiesChromatographic PrinciplesPrediction of Peptide Retention TimesAdvantages of Reduced ScaleTwo-Dimensional Chromatographic MethodsPeptide Analysis in Complex Biological MatricesStandard Methods for Peptide Separations for Analysis by Hyphenated TechniquesEmerging Methods for Peptide Separations for Analysis by Hyphenated TechniquesPractical Use of RP-HPLC for Purifying Peptides (Analytical and Preparative Scale)DIFFICULT PEPTIDESImportance of Peptide SynthesisMethods for Peptide SynthesisChemical Peptide Synthesis"Difficult Peptide Sequences"Means to Overcome Peptide Aggregation in SPPSMonitoring the Synthesis of a "Difficult Peptide"Conclusions
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Autoren-Porträt
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.
Bibliographische Angaben
- 2010, XX, 584 Seiten, 6 farbige Abbildungen, 385 Schwarz-Weiß-Abbildungen, Maße: 17,7 x 24,8 cm, Gebunden, Englisch
- Herausgegeben: Andrew B. Hughes
- Verlag: Wiley-VCH
- ISBN-10: 3527321020
- ISBN-13: 9783527321025
- Erscheinungsdatum: 15.12.2010
Sprache:
Englisch
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