Amino Acids Peptides and Proteins in Organic Chemistry 1 Origins and Synthesis of Amino Acids Amino Acids Peptides and Proteins in Organic Chemistry VCH 1st Edition by Andrew B. Hughes – Ebook PDF Instant Download/Delivery: 9783527320967, 3527320962
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Product details:
ISBN 10: 3527320962
ISBN 13: 9783527320967
Author: Andrew B. Hughes
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.
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
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 purification and automation.
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.
Table of contents:
Part One: Origins of Amino Acids
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Extraterrestrial Amino Acids
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Z. Martins and M.A. Sephton
1.1 Introduction
1.2 ISM
1.3 Comets
1.4 Meteorites
1.5 Micrometeorites and IDPs
1.6 Mars
1.7 Delivery of Extraterrestrial Amino Acid to the Earth and its Importance to the Origin of Life
1.8 Conclusions
References
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“Terrestrial” Amino Acids and their Evolution
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Stephen Freeland
2.1 Introduction
2.2 What are the 20 “Terrestrial” Amino Acids?
2.3 What do We Know about the Evolution of the Standard Amino Acid Alphabet?
2.4 Amino Acids that Life Passed Over: A Role for Natural Selection?
2.5 Why Does Life Genetically Encode L-Amino Acids?
2.6 Summary, Synthesis, and Conclusions
References
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Part Two: Production/Synthesis of Amino Acids
3. Use of Enzymes in the Synthesis of Amino Acids
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Theo Sonke, Bernard Kaptein, and Hans E. Schoemaker
3.1 Introduction
3.2 Chemo-Enzymatic Processes to Enantiomerically Pure Amino Acids
3.3 Acylase Process
3.4 Amidase Process
3.5 Hydantoinase Process
3.6 Ammonia Lyase Processes
3.7 Aminotransferase Process
3.8 AADH Process
3.9 Conclusions
References
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b-Amino Acid Biosynthesis
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Peter Spiteller
4.1 Introduction
4.2 Biosynthesis of b-Amino Acids
4.3 Conclusions and Future Prospects
References
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Methods for the Chemical Synthesis of Noncoded a-Amino Acids found in Natural Product Peptides
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Stephen A. Habay, Steve S. Park, Steven M. Kennedy, and A. Richard Chamberlin
5.1 Introduction
5.2 Noncoded CAAs
5.3 Noncoded Amino Acids by Chemical Modification of Coded Amino Acids
5.4 Noncoded Amino Acids with Elaborate Side-Chains
5.5 Conclusions
References
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Synthesis of N-Alkyl Amino Acids
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Luigi Aurelio and Andrew B. Hughes
6.1 Introduction
6.2 N-Methylation via Alkylation
6.3 N-Methylation via Schiff’s Base Reduction
6.4 N-Methylation by Novel Methods
6.5 N-Alkylation of Amino Acids
References
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Recent Developments in the Synthesis of b-Amino Acids
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Yamir Bandala and Eusebio Juaristi
7.1 Introduction
7.2 Synthesis of b-Amino Acids by Homologation of a-Amino Acids
7.3 Chiral Pool: Enantioselective Synthesis of b-Amino Acids from Aspartic Acid, Asparagine, and Derivatives
7.4 Synthesis of b-Amino Acids by Conjugate Addition of Nitrogen Nucleophiles to Enones
7.5 Synthesis of b-Amino Acids via 1,3-Dipolar Cycloaddition
7.6 Synthesis of b-Amino Acids by Nucleophilic Additions
7.7 Synthesis of b-Amino Acids by Diverse Addition or Substitution Reactions
7.8 Synthesis of b-Amino Acids by Stereoselective Hydrogenation of Prochiral 3-Aminoacrylates and Derivatives
7.9 Synthesis of b-Amino Acids by use of Chiral Auxiliaries: Stereoselective Alkylation
7.10 Synthesis of b-Amino Acids via Radical Reactions
7.11 Miscellaneous Methods for the Synthesis of b-Amino Acids
7.12 Conclusions
7.13 Experimental Procedures
References
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Synthesis of Carbocyclic b-Amino Acids
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Loránd Kiss, Enikő Forró, and Ferenc Fülöp
8.1 Introduction
8.2 Synthesis of Carbocyclic b-Amino Acids
8.3 Synthesis of Functionalized Carbocyclic b-Amino Acid Derivatives
8.4 Enzymatic Routes to Carbocyclic b-Amino Acids
8.5 Conclusions and Outlook
8.6 Experimental Procedures
References
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Synthetic Approaches to a,b-Diamino Acids
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Alma Viso and Roberto Fernández de la Pradilla
9.1 Introduction
9.2 Construction of the Carbon Backbone
9.3 Introduction of the Nitrogen Atoms in the Carbon Backbone
9.4 Conclusions
9.5 Experimental Procedures
References
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Synthesis of Halogenated a-Amino Acids
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Madeleine Strickland and Christine L. Willis
10.1 Introduction
10.2 Halogenated Amino Acids with a Hydrocarbon Side-Chain
10.3 Halogenated Amino Acids with an Aromatic Side-Chain
10.4 Halogenated Amino Acids with Heteroatoms in the Aliphatic Side-Chain
References
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Synthesis of Isotopically Labeled a-Amino Acids
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Caroline M. Reid and Andrew Sutherland
11.1 Introduction
11.2 Enzyme-Catalyzed Methods
11.3 Chiral Pool Approach
11.4 Chemical Asymmetric Methods
11.5 Conclusions
11.6 Experimental Procedures
References
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Synthesis of Unnatural/Nonproteinogenic a-Amino Acids
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David J. Ager
12.1 Introduction
12.2 Chemical Methods
12.3 Enzymatic Methods
12.4 Conclusions
12.5 Experimental Procedures
References
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Synthesis of g- and d-Amino Acids
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Andrea Trabocchi, Gloria Menchi, and Antonio Guarna
13.1 Introduction
13.2 g-Amino Acids
13.3 d-Amino Acids
13.4 Conclusions
References
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Synthesis of g-Aminobutyric Acid Analogs
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Jane R. Hanrahan and Graham A.R. Johnston
14.1 Introduction
14.2 a-Substituted g-Amino Acids
14.3 b-Substituted g-Amino Acids
14.4 g-Substituted g-Amino Acids
14.5 Halogenated g-Amino Acids
14.6 Disubstituted g-Amino Acids
14.7 Trisubstituted g-Amino Acids
14.8 Hydroxy-g-Amino Acids
14.9 Unsaturated g-Amino Acids
14.10 Cyclic g-Amino Acids
14.11 Conclusions
14.12 Experimental Procedures
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Tags: Andrew Hughes, Amino Acids, Peptides and Proteins, Organic Chemistry


