Beschreibung:
This is the fourth 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 "e;who's who"e; 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. The 5 volumes cover the following topics: Volume 1: Origins and Synthesis of Amino Acids Volume 2: Modified Amino Acids, Organocatalysis and Enzymes Volume 3: Building Blocks, Catalysis and Coupling Chemistry Volume 4: Protection Reactions, Medicinal Chemistry, Combinatorial Synthesis Volume 5: Analysis and Function of Amino Acids and Peptides The fourth volume in this series is structured in three main sections. The first section is about protection reactions and amino acid based peptidomimetics. The second, and most extensive, part is devoted to the medicinal chemistry of amino acids. It includes, among others, the chemistry of alpha- and beta amino acids, peptide drugs, and advances in N- and O-glycopeptide synthesis. The final part deals with amino acids in combinatorial synthesis. Methods, such as phage display, library peptide synthesis, and computational design are described. Originally planned as a six volume series, Amino Acids, Peptides and Proteins in Organic Chemistry now completes with five volumes but remains comprehensive in both scope and coverage. Further information about the 5 Volume Set and purchasing details can be viewed here.
This is the fourth 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.The fourth volume in this five-volume series is structured in three main sections. The first section is about protection reactions and amino acid-based peptidomimetics. The second, and most extensive, part is devoted to the medicinal chemistry of amino acids. It includes, among others, the chemistry of alpha- and beta amino acids, peptide drugs, and advances in N- and O-glycopeptide synthesis. The final part deals with amino acids in combinatorial synthesis. Methods, such as phage display, library peptide synthesis, and computational design are described.
PROTECTION REACTIONSGeneral ConsiderationsAlpha-Amino Protection (Nalpha-Protection)Carboxy ProtectionSide Chain ProtectionPhotocleavable ProtectionsConclusionsExperimental ProceduresPART I: Amino Acid-Based PeptidomimeticsTHE HUISGEN CYCLOADDITION IN PEPTIDOMIMETIC CHEMISTRYIntroductionHuisgen [2+3] Cycloaddition Between Azides and AcetylenesMechanistic Consideration for the Cu-Huisgen and Ru-Huisgen CycloadditionBuilding Blocks for the Synthesis of TriazoleModified PeptidomimeticsCyclic Triazole PeptidomimeticsAcylic Triazole PeptidomimeticsUseful Experimental ProceduresRECENT ADVANCES IN BETA-STRAND MIMETICSIntroductionMacrocyclic PeptidomimeticsAcyclic CompoundsAliphatic and Aromatic CarbocyclesLigands Containing One Ring with One Heteroatom (N)Ligands Containing One Ring or Multiple Rings with One Heteroatom (O,S)Ligands Containing One Ring with Two Heteroatoms (N,N)Ligands Containing One Ring with Two Heteroatoms (N,S) or Three Heteroatoms (N,N,S or N,N,N)Ligands Containing Two Rings with One Heteroatom (N or O)Ligands Containing Two Rings with Two or Three Heteroatoms (N,N or N,S or N,N,N)ConclusionsPART II: Medicinal Chemistry of Amino AcidsMEDICINAL CHEMISTRY OF ALPHA-AMINO ACIDSIntroductionGlutamic AcidConformational RestrictionBioisosterismStructure-Activity-StudiesConclusionsMEDICINAL CHEMISTRY OF ALICYCLIC BETA-AMINO ACIDSIntroductionFive-Membered Alicyclic Beta-Amino AcidsSix-Membered Alicyclic Beta-Amino AcidsMEDICINAL CHEMISTRY OF ALPHA-HYDROXY-BETA-AMINO ACIDSIntroductionAlpha-Hydroxy-Beta-Amino AcidsAntibacterial AgentsInhibitors of AminopeptidasesAspartyl Proteases InhibitorsPaclitaxel and its DerivativesPEPTIDE DRUGSLights and Shades of Peptide and Protein DrugsPeptide Drugs Available on the MarketApproved Peptides in OncologyAntimicrobial PeptidesPerspectivesORAL BIOAVAILABILITY OF PEPTIDE AND PEPTIDOMIMETIC DRUGSIntroductionFundamental Considerations of Intestinal AbsorptionBarriers Limiting Oral Peptide/Peptidomimetic Drug BioavailabilityStrategies to Improve Oral Bioavailability of Peptide-Based DrugsConclusionsASYMMETRIC SYNTHESIS OF BETA-LACTAMS VIA THE STAUDINGER REACTIONIntroductionStaudinger ReactionInfluence of the Geometry of the Imine on Stereoselectivity in the ReactionInfluence of the Polarity of the Solvent on Stereoselectivity of the ReactionInfluence of the Isomerization of the Imine Prior to its Nucleophilic Attack onto the Ketene Stereoselectivity in the ReactionInfluence of the Order of Addition of the Reactants to the ReactionInfluence of Chiral Substituents on the Stereoselectivity of the ReactionAsymmetric Induction from the Imine ComponentAsymmetric Induction from the Ketene ComponentDouble Asymmetric CycloinductionInfluence of Catalysts on the Stereoselectivity of the ReactionConcludingsADVANCES IN N- AND O-GLYCOPEPTIDE SYNTHESIS - A TOOL TO STUDY CLYCOSYLATION AND DEVELOP NEW THERAPEUTICSIntroductionSynthesis of O-GlycopeptidesSynthesis of N-GlycopeptidesRECENT DEVELOPMENTS IN NEOGLYCOPEPTIDE SYNTHESISIntroductionNeoglycoside and Neoglycopeptide SynthesisProtein Side-Chain ModificationsCu(I)-Catalyzed Azide-Alkyne "Click" CycloadditionCross-MetathesisApplication of Neoglycopeptides as Synthetic VaccinesEnzymatic, Molecular and Cell Biological TechniquesPART III: Amino Acids in Combinatorial SynthesisCOMBINATORIAL/LIBRARY PEPTIDE SYNTHESISIntroductionHigh-Throughput Synthesis of PeptidesSynthesis of Peptide ArraysPeptide LibrariesFuture of Peptide LibrariesSynthetic ProtocolsPHAGE-DISPLAYED COMBINATORIAL PEPTIDESIntroductionConclusionsDESIGNING NEW PROTEINSIntroductionProtein Design MethodsProtocol for Protein DesignConclusionsAMINO ACID-BASED DENDRIMERSIntroductionPeptide Dendrimer Synthesis: Divergent and Convergent ApproachesApplications of Peptide DendrimersConclusions