Chemistry of peptide synthesis. ([2016?])

• Record Type: Book
• Further Information: Note: N. Leo Benoiton.
• Authors: Benoiton, N. Leo
• Contents: 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; Polystyre
• Publisher Details: Boca Raton : CRC Press
• Publication Date: 2016
• Copyright Date: 2006
• Extent: 1 online resource
• Subjects: 612.015756; Peptides -- Synthesis; Peptides -- chemical synthesis; MEDICAL -- Biochemistry; Peptides -- Synthesis; Electronic books; Electronic books
• Languages: English
• ISBNs: 9781420027693; 1420027697
• Related ISBNs: 9781574444544; 1574444549
• Notes: Note: Includes bibliographical references and index.
• Access Rights: Legal Deposit; Only available on premises controlled by the deposit library and to one user at any one time; The Legal Deposit Libraries (Non-Print Works) Regulations (UK).
• Access Usage: Restricted: Printing from this resource is governed by The Legal Deposit Libraries (Non-Print Works) Regulations (UK) and UK copyright law currently in force.