Amino Acids, Peptides and Proteins in Organic Chemistry: Volume 1 - Origins and Synthesis of Amino Acids

Closing a gap in the literature, this is the only book 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, this series is 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.

List of Contributors.
Part One Origins of Amino Acids.

1 Extraterrestrial Amino Acids (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.

2 ‘‘Terrestrial’’ Amino Acids and their Evolution (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.

Part Two Production/Synthesis of Amino Acids.

3 Use of Enzymes in the Synthesis of Amino Acids (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.

4 b-Amino Acid Biosynthesis (Peter Spiteller).

4.1 Introduction.

4.2 Biosynthesis of b-Amino Acids.

4.3 Conclusions and Future Prospects.

References.

5 Methods for the Chemical Synthesis of Noncoded a-Amino Acids found in Natural Product Peptides (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.

6 Synthesis of N-Alkyl Amino Acids (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.

7 Recent Developments in the Synthesis of b-Amino Acids (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.

8 Synthesis of Carbocyclic β-Amino Acids (Loránd Kiss, EnikőForró, and Ferenc Fülöp).

8.1 Introduction.

8.2 Synthesis of Carbocyclic β-Amino Acids.

8.3 Synthesis of Functionalized Carbocyclic β-Amino Acid Derivatives.

8.4 Enzymatic Routes to Carbocyclic β-Amino Acids.

8.5 Conclusions and Outlook.

8.6 Experimental Procedures.

References.

9 Synthetic Approaches to α,β-Diamino Acids (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.

10 Synthesis of Halogenated α-Amino Acids (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.

11 Synthesis of Isotopically Labeled α-Amino Acids (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.

12 Synthesis of Unnatural/Nonproteinogenic α-Amino Acids (David J. Ager).

12.1 Introduction.

12.2 Chemical Methods.

12.3 Enzymatic Methods.

12.4 Conclusions.

12.5 Experimental Procedures.

References.

13 Synthesis of γ- and б-Amino Acids (Andrea Trabocchi, Gloria Menchi, and Antonio Guarna).

13.1 Introduction.

13.2 γ-Amino Acids.

13.3 б-Amino Acids.

13.4 Conclusions.

References.

14 Synthesis of γ-Aminobutyric Acid Analogs (Jane R. Hanrahan and Graham A.R. Johnston).

14.1 Introduction.

14.2 α-Substituted γ-Amino Acids.

14.3 β-Substituted γ-Amino Acids.

14.4 γ-Substituted γ-Amino Acids.

14.5 Halogenated γ-Amino Acids.

14.6 Disubstituted γ-Amino Acids.

14.7 Trisubstituted γ-Amino Acids.

14.8 Hydroxy-γ-Amino Acids.

14.9 Unsaturated γ-Amino Acids.

14.10 Cyclic γ-Amino Acids.

14.11 Conclusions.

14.12 Experimental Procedures.

References.

Index.


Andrew Hughes is a Reader and Head of the Department of Chemistry, La Trobe University, Melbourne, Australia. He obtained his degrees from the University of Western Australia before taking up post-doctoral appointments at the University of Cambridge starting 1989. After three years working with Professor Andrew Holmes, he joined Professor Steven Ley's group in 1993. While at Cambridge he was appointed the Shell Research Fellow at Robinson College. His interests lie in the general field of asymmetric synthesis and methodology, with a recent focus on amino acid chemistry.

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