Peptide chemistry : a practical textbook

書誌事項

Peptide chemistry : a practical textbook

Miklos Bodanszky

Springer, c1993

2nd rev. ed

  • : gw
  • : us

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注記

Includes bibliographical references and index

内容説明・目次

内容説明

A continued interest in Peptide Chemistry prompted the revision of the first edition of this book. This provided an opportunity to update several details. I am grateful to colleagues who were kind enough to inform me of errors, typographical and other, they had discovered in the first edi- tion. These have now been corrected, as were certain shortcomings in language and style pointed out by my daughter, Dr. Eva Bodanszky. In 1991 the excellent The Chemical Synthesis of Peptides by John Jones (Oxford University Press, 1991) appeared. It covers, in part, the same field, but is different enough from Peptide Chemistry, to justify publication of a revised edition of the latter. Princeton, July 1993 M. Bodanszky Preface to the First Edition Nature applied peptides for a great variety of specific functions. The specificity provided by the individual character of each amino acid is further ehanced by the combination of several amino acids into larger molecules. Peptides therefore can act as chemical messengers, neuro- transmitters, as highly specific stimulators and inhibitors, regulating var- ious life-processes. Entire classes of biologically active compounds, such as the opioid peptides or the gastrointestinal hormones emerged within short periods of time and it is unlikely that the rapid succession of discoveries of important new peptides would come to a sudden halt. In fact, our knowledge of the field is probably still in an early stage of development. Peptides also gained importance in our everyday life.

目次

I. Introduction.- References and Additional Sources.- One: Structure Determination.- II. Amino Acid Analysis.- Additonal Sources.- III. Sequence Determination.- A. End Group Determination.- 1. Determination of the N-terminal Residue.- 2. Determination of the C-terminal Residue.- B. Sequential Degradation.- 1. Hydrolysis Catalyzed by Exopeptidases.- 2. Edman Degradation.- a) The Two-step Procedure.- b) The Three-step Procedure.- c) Automated Sequencing.- d) The Edman-Dansyl Process.- C. Sequence Determination with the Help of Mass Spectra.- D. Fragmentation of Peptides.- 1. Hydrolysis with Specific Endopeptidases.- 2. Chemical Methods of Cleavage.- 3. Fission of Disulfides.- References and Additional Sources.- IV. Secondary and Tertiary Structure.- A. Architectural Features in Peptides.- 1. The Peptide Bond.- 2. Secondary Structures.- 3. Tertiary Structure.- 4. Quaternary Structure.- B. Methods for the Analysis of Conformation of Peptides.- 1. Optical Rotatory Dispersion and Circular Dichroism.- 2. Nuclear Magnetic Resonance (nmr) Spectroscopy.- 3. X-Ray Crystallography.- C. Prediction of Conformation in Peptides.- References and Additional Sources.- Two: Peptide Synthesis.- V. Formation of the Peptide Bond.- A. The Acid Chloride Method.- B. The Acid Azide Method.- C. Anhydrides.- D. Active Esters.- E. Coupling Reagents.- F. Enzyme-catalyzed Bond Formation.- G. Non-conventional Methods of Peptide Bond Formation.- References.- Additional Sources.- VI. Protection of Functional Groups.- A. Blocking of ?-Amino Groups.- B. Blocking of Side Chain Amino Groups.- C. Protection of the Carboxyl Group.- D. Protection of Hydroxyl Groups.- E. Blocking of the Sulfhydryl Group.- F. Masking the Thioether in Methionine.- G. Protection of the Guanidine Function in the Arginine Side Chain.- H. Masking the Imidazole in Histidine.- I. Indole Protection.- J. Carboxamide Blocking Groups.- References and Additional Sources.- VII. Undesired Reactions During Synthesis.- A. Base-catalyzed Ring Closure.- B. Acid-catalyzed Ring Closure.- C. Acyl Migration.- D. Alkylation.- E. Friedel-Crafts Reaction.- F. Saturation of Aromatic Nuclei.- G. Reductive Cleavage of the Peptide Chain.- H. Oxidative Decomposition of the Indole in Tryptophan.- I. Side Reactions Caused by Steric Hindrance.- J. Prevention and Suppression of Side Reactions.- Additional Source.- VIII. Racemization.- A. Mechanism of Racemization.- B. Detection of Racemization.- C. Racemization Studies in Model Systems.- D. Prevention of Racemization.- References and Additional Source.- IX. Design of Schemes for Peptide Synthesis.- A. Segment Condensation.- B. Stepwise Chain-lengthening Starting with the N-Terminal Residue.- C. Stepwise Chain-lengthening Starting with the C-Terminal Residue.- D. Tactical Considerations.- E. Synthesis of Special Target Peptides.- 1. Polyamino Acids and Sequential Polypeptides.- 2. Disulfide Bridges.- 3. Cyclic Peptides.- 4. Peptides Containing Non-amino Acid Constituents.- 5. Semisynthesis (Partial Synthesis).- References.- Additional Sources.- X. Solid Phase Peptide Synthesis.- A. The Insoluble Polymeric Support and the Bond Linking the Peptide to the Resin.- B. Removal of Temporary Blocking Groups.- C. Coupling: Acylation of the Resin-bound Amine-component.- D. Separation of the Completed Peptide Chain from the Polymeric Support and Final Deprotection.- E. Some Problems Encountered in Solid Phase Peptide Synthesis.- 1. Premature Chain-termination.- 2. Deletion.- References and Additional Sources.- XI. Methods of Facilitation.- A. Chains Attached to a Soluble Polymer (The Liquid Phase Method).- B. The Picolyl Ester Method.- C. Rapid Synthesis.- 1. Chain-building Without Isolation of Intermediates.- 2. Chain-building Through Isolated Intermediates.- D. Synthesis "in situ".- E. Simultaneous Synthesis of Peptide Analogs.- F. Insoluble Reagents.- 1. Active Esters.- 2. Polymeric Coupling Reagents.- 3. Insoluble Cleaving Reagents.- References and Additional Sources.- XII. Analysis and Characterization of Synthetic Peptides.- A. Homogeneity Tests.- B. Amino Acid Analysis and Sequence Determination.- C. Elemental Analysis.- D. Measurement of Optical Activity.- E. Infrared and Ultraviolet Absorption Spectra.- F. Nuclear Magnetic Resonance Spectra.- G. Molecular-weight Determination.- Reference and Additional Sources.

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