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Chemistry of Peptide Synthesis
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FUNDAMENTALS OF PEPTIDE SYNTHESIS Chemical and Stereochemical Nature of Amino Acids Ionic Nature of Amino Acids Charged Groups in Peptides at Neutral pH Side-Chain Effects in Other Amino Acids General Approach to Protection and Amide-Bond Formation N-Acyl and Urethane-Forming N-Substituents Amide-Bond Formation and the Side Reaction of Oxazolone Formation Oxazolone Formation and Nomenclature Coupling, 2-Alkyl-5(4H)-Oxazolone Formation and Generation of Diastereoisomers from Activated Peptides Coupling of N-Alkoxycarbonylamino Acids without Generation of Diastereoisomers: Chirally Stable 2-Alkoxy-5(4H)-Oxazolones Effects of the Nature of the Substituents on the Amino and Carboxyl Groups of the Residues that are Coupled to Produce a Peptide Introduction to Carbodiimides and Substituted Ureas Carbodiimide-Mediated Reactions of N-Alkoxycarbonylamino Acids Carbodiimide-Mediated Reactions of N-Acylamino Acids and Peptides Preformed Symmetrical Anhydrides of N-Alkoxycarbonylamino Acids Purified Symmetrical Anhydrides of N-Alkoxycarbonylamino Acids Obtained Using a Soluble Carbodiimide Purified 2-Alkyl-5(4H)-Oxazolones from N-Acylamino and N-Protected Glycylamino Acids 2-Alkoxy-5(4H)-Oxazolones as Intermediates in Reactions of N-Alkoxycarbonylamino Acids Revision of the Central Tenet of Peptide Synthesis Strategies for the Synthesis of Enantiomerically Pure Peptides Abbreviated Designations of Substituted Amino Acids and Peptides Literature on Peptide Synthesis METHODS FOR THE FORMATION OF PEPTIDE BONDS Coupling Reagents and Methods and Activated Forms Peptide-Bond Formation from Carbodiimide-Mediated Reactions of N-Alkoxycarbonylamino Acids Factors Affecting the Course of Events in Carbodiimide-Mediated Reactions of N-Alkoxycarbonylamino Acids Intermediates and Their Fate in Carbodiimide-Mediated Reactions of N-Alkoxycarbonylamino Acids Peptide-Bond Formation from Preformed Symmetrical Anhydrides of N-Alkoxycarbonylamino Acids Peptide-Bond Formation from Mixed Anhydrides of N-Alkoxycarbonylamino Acids Alkyl Chloroformates and Their Nomenclature Purified Mixed Anhydrides of N-Alkoxycarbonylamino Acids and Their Decomposition to 2-Alkoxy-5(4H)-Oxazolones Peptide-Bond Formation from Activated Esters of N-Alkoxycarbonylamino Acids Anchimeric Assistance in the Aminolysis of Activated Esters On the Role of Additives as Auxiliary Nucleophiles: Generation of Activated Esters 1-Hydroxybenzotriazole as an Additive that Suppresses N-Acylurea Formation by Protonation of the O-Acylisourea Peptide-Bond Formation from Azides of N-Alkoxycarbonylamino Acids Peptide-Bond Formation from Chlorides of N-Alkoxycarbonylamino Acids: N-9-Fluorenylmethoxycarbonylamino-Acid Chlorides Peptide-Bond Formation from 1-Ethoxycarbonyl-2-Ethoxy-1,2-Dihydroquinoline-Mediated Reactions of N-Alkoxycarbonylamino Acids Coupling Reagents Composed of an Additive Linked to a Charged Atom Bearing Dialkylamino Substituents and a Nonnucleophilic Counter-Ion Peptide-Bond Formation from Benzotriazol-1-yl-Oxy-tris(Dimethylamino)Phosphonium Hexafluorophosphate-Mediated Reactions of N-Alkoxycarbonylamino Acids Peptide-Bond Formation from O-Benzotriazol-1-yl-N,N,N',N' TetramethyluroniumHexafluorophosphate- and Tetrafluoroborate-Mediated Reactions of N-Alkoxycarbonylamino Acids Pyrrolidino Instead of Dimethylamino Substituents for the Environmental Acceptability of Phosphonium and Carbenium Salt-Based Reagents Intermediates and Their Fate in Benzotriazol-1-yl-Oxyphosphonium and Carbenium Salt-Mediated Reactions 1-Hydroxybenzotriazole as Additive in Couplings of N-Alkoxycarbonylamino Acids Effected by Phosphonium and Uronium Salt-Based Reagents Some Tertiary Amines Used as Bases in Peptide Synthesis The Applicability of Peptide-Bond Forming Reactions to the Coupling of N-Protected Peptides Is Dictated by the Requirement to Avoid Epimerization: 5(4H)-Oxazolones from Activated Peptides Methods for Coupling N-Protected Peptides On the Role of 1-Hydroxybenzotriazole as an Epimerization Suppressant in Carbodiimide-Mediated Reactions More on Additives An Aid to Deciphering the Constitution of Coupling Reagents from Their Abbreviations PROTECTORS AND METHODS OF DEPROTECTION The Nature and Properties Desired of Protected Amino Acids Alcohols from which Protectors Derive and Their Abbreviated Designations Deprotection by Reduction: Hydrogenolysis Deprotection by Reduction: Metal-Mediated Reactions Deprotection by Acidolysis: Benzyl-Based Protectors Deprotection by Acidolysis:tert-Butyl-Based Protectors Alkylation due to Carbenium Ion Formation during Acidolysis Deprotection by Acid-Catalyzed Hydrolysis Deprotection by Base-Catalyzed Hydrolysis Deprotection by beta-Elimination Deprotection by beta-Elimination: 9-Fluorenylmethyl-Based Protectors Deprotection by Nucleophilic Substitution by Hydrazine or Alkyl Thiols Deprotection by Palladium-Catalyzed Allyl Transfer Protection of Amino Groups: Acylation and Dimer Formation Protection of Amino Groups: Acylation without Dimer Formation Protection of Amino Groups: tert-Butoxycarbonylation Protection of Carboxyl Groups: Esterification Protection of Carboxyl, Hydroxyl, and Sulfhydryl Groups by tert-Butylation and Alkylation Protectors Sensitized or Stabilized to Acidolysis Protecting Group Combinations CHIRALITY IN PEPTIDE SYNTHESIS Mechanisms of Stereomutation: Acid-Catalyzed Enolization Mechanisms of Stereomutation: Base-Catalyzed Enolization Enantiomerization and Its Avoidance during Couplings of N-Alkoxycarbonyl-L-Histidine Mechanisms of Stereomutation: Base-Catalyzed Enolization of Oxazolones Formed from Activated Peptides Mechanisms of Stereomutation: Base-Induced Enolization of Oxazolones Formed from Activated N-Alkoxycarbonylamino Acids Stereomutation and Asymmetric Induction Terminology for Designating Stereomutation Evidence of Stereochemical Inhomogeneity in Synthesized Products Tests Employed to Acquire Information on Stereomutation Detection and Quantitation of Epimeric Peptides by NMR Spectroscopy Detection and Quantitation of Epimeric Peptides by HPLC External Factors that Exert an Influence on the Extent of Stereomutation During Coupling Constitutional Factors that Define the Extent of Stereomutation During Coupling: Configurations of the Reacting Residues Constitutional Factors that Define the Extent of Stereomutation During Coupling: The N-Substituent of the Activated Residue or the Penultimate Residue Constitutional Factors that Define the Extent of Stereomutation During Coupling: The Aminolyzing Residue and its Carboxy Substituent Constitutional Factors that Define the Extent of Stereomutation During Coupling: The Nature of the Activated Residue Reactions of Activated Forms of N-Alkoxycarbonylamino Acids in the Presence of Tertiary Amine Implications of Oxazolone Formation in the Couplings of N-Alkoxycarbonlyamino Acids in the Presence of Tertiary Amine Enantiomerization in 4-Dimethylaminopyridine-Assisted Reactions of N-Alkoxycarbonylamino Acids Enantiomerization During Reactions of Activated N-Alkoxycarbonylamino Acids with Amino Acid Anions Possible Origins of Diastereomeric Impurities in Synthesized Peptides Options for Minimizing Epimerization during the Coupling of Segments Methods for Determining Enantiomeric Content Determination of Enantiomers by Analysis of Diastereoisomers Formed by Reaction with a Chiral Reagent SOLID-PHASE SYNTHESIS The Idea of Solid-Phase Synthesis Solid-Phase Synthesis as Developed by Merrifield Vessels and Equipment for Solid-Phase Synthesis A Typical Protocol for Solid-Phase Synthesis Features and Requirements for Solid-Phase Synthesis Options and Considerations for Solid-Phase Synthesis Polystyrene Resins and Solvation in Solid-Phase Synthesis Polydimethylacrylamide Resin Polyethyleneglycol-Polystyrene Graft Polymers Terminology and Options for Anchoring the First Residue Types of Target Peptides and Anchoring Linkages Protecting Group Combinations for Solid-Phase Synthesis Features of Synthesis Using Boc/Bzl Chemistry Features of Synthesis Using Fmoc/tBu Chemistry Coupling Reagents and Methods for Solid-Phase Synthesis Merrifield Resin for Synthesis of Peptides Using Boc/Bzl Chemistry Phenylacetamidomethyl Resin for Synthesis of Peptides Using Boc/Bzl Chemistry Benzhydrylamine Resin for Synthesis of Peptide Amides Using Boc/Bzl Chemistry Resins and Linkers for Synthesis of Peptides Using Fmoc/tBu Chemistry Resins and Linkers for Synthesis of Peptide Amides Using Fmoc/tBu Chemistry Resins and Linkers for Synthesis of Protected Peptide Acids and Amides Esterification of Fmoc-Amino Acids to Hydroxymethyl Groups of Supports 2-Chlorotrityl Chloride Resin for Synthesis Using Fmoc/tBu Chemistry Synthesis of Cyclic Peptides on Solid Supports REACTIVITY, PROTECTION, AND SIDE REACTIONS Protection Strategies and the Implications Thereof Constitutional Factors Affecting the Reactivity of Functional Groups Constitutional Factors Affecting the Stability of Protectors The e-Amino Group of Lysine The Hydroxyl Groups of Serine and Threonine Acid-Induced O-Acylation of Side-Chain Hydroxyls and the O-to-N Acyl Shift The Hydroxyl Group of Tyrosine The Methylsulfanyl Group of Methionine The Indole Group of Tryptophan The Imidazole Group of Histidine The Guanidino Group of Arginine The Carboxyl Groups of Aspartic and Glutamic Acids Imide Formation from Substituted Dicarboxylic Acid Residues The Carboxamide Groups of Asparagine and Glutamine Dehydration of Carboxamide Groups to Cyano Groups During Activation Pyroglutamyl Formation from Glutamyl and Glutaminyl Residues The Sulfhydryl Group of Cysteine and the Synthesis of Peptides Containing Cystine Disulfide Interchange and Its Avoidance during the Synthesis of Peptides Containing Cystine Piperazine-2,5-Dione Formation from Esters of Dipeptides N-Alkylation during Palladium-Catalyzed Hydrogenolytic Deprotection and Its Synthetic Application Catalytic Transfer Hydrogenation and the Hydrogenolytic Deprotection of Sulfur-Containing Peptides Mechanisms of Acidolysis and the Role of Nucleophiles Minimization of Side Reactions during Acidolysis Trifunctional Amino Acids with Two Different Protectors VENTILATION OF ACTIVATED FORMS AND COUPLING METHODS Notes on Carbodiimides and Their Use Cupric Ion as an Additive that Eliminates Epimerization in Carbodiimide-Mediated Reactions Mixed Anhydrides: Properties and Their Use Secondary Reactions of Mixed Anhydrides: Urethane Formation Decomposition of Mixed Anhydrides: 2-Alkoxy-5(4H)-Oxazolone Formation and Disproportionation Activated Esters: Reactivity Preparation of Activated Esters using Carbodiimides and Associated Secondary Reactions Other Methods for the Preparation of Activated Esters of N-Alkoxycarbonylamino Acids Activated Esters: Properties and Specific Uses Methods for the Preparation of Activated Esters of Protected Peptides, Including Alkyl Thioesters Synthesis using N-9-Fluorenylmethoxycarbonylamino Acid Chlorides Synthesis using N-Alkoxycarbonylamino-Acid Fluorides Amino-Acid N-Carboxyanhydrides: Preparation and Aminolysis N-Alkoxycarbonylamino-Acid N-Carboxyanhydrides Decomposition during the Activation of Boc-Amino Acids and Consequent Dimerization Acyl Azides and the Use of Protected Hydrazides O-Acyl and N-Acyl N'-Oxide Forms of 1-Hydroxybenzotriazole Adducts and the Uronium and Guanidinium Forms of Coupling Reagents Phosphonium and Uronium/Aminium/Guanidinium Salt-Based Reagents: Properties and Their Use Newer Coupling Reagents To Preactivate or not to Preactivate: Should That Be the Question? Aminolysis of Succinimido Esters by Unprotected Amino Acids or Peptides Unusual Phenomena Relating to Couplings of Proline Enantiomerization of the Penultimate Residue During Coupling of an N-Protected Peptide Double Insertion in Reactions of Glycine Derivatives: Rearrangement of Symmetrical Anhydrides to Peptide-Bond-Substituted Dipeptides Synthesis of Peptides by Chemoselective Ligation Detection and Quantitation of Activated Forms MISCELLANEOUS Enantiomerization of Activated N-Alkoxycarbonylamino Acids and Esterified Cysteine Residues in the Presence of Base Options for Preparing N-Alkoxycarbonylamino Acid Amides and 4-Nitroanilides Options for Preparing Peptide Amides Aggregation during Peptide-Chain Elongation and Solvents for its Minimization Alkylation of Peptide Bonds to Decrease Aggregation: 2-Hydroxybenzyl Protectors Alkylation of Peptide Bonds to Decrease Aggregation: Oxazolidines and Thiazolidines (Pseudo-Prolines) Capping and the Purification of Peptides Synthesis of Large Peptides in Solution Synthesis of Peptides in Multikilogram Amounts Dangers and Possible Side Reactions Associated with the Use of Reagents and Solvents Organic and Other Salts in Peptide Synthesis Reflections on the Use of Tertiary and Other Amines Monomethylation of Amino Groups and the Synthesis of N-Alkoxycarbonyl-N-Methylamino Acids The Distinct Chiral Sensitivity of N-Methylamino Acid Residues and Sensitivity to Acid of Adjacent Peptide Bonds Reactivity and Coupling at -Methylamino Acid Residues APPENDICES Useful Reviews Year, Location and Chairmen of the Major Symposia On the "Primary Sequence" of Peptides and Proteins Index

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