Amino Acids, Peptides and Proteins in Organic Chemistry

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. 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.

PART I: Origins of Amino Acids

EXTRATERRESTRIAL AMINO ACIDS
Introduction
ISM
Comets
Meteorites
Micrometeorites and IDPs
Mars
Delivery of Extraterrestrial Amino Acid to the Earth and its Importance to the Origin of Life
"TERRESTRIAL" AMINO ACIDS AND THEIR EVOLUTION
Introduction
What are the 20 "Terrestrial" Amino Acids?
What do We Know about the Evolution of the Standard Amino Acid Alphabet?
Amino Acids that Life Passed Over: A Role for Natural Selection?
Why Does Life Genetically Encode L-Amino Acids?
Summary, Synthesis, and Conclusions

PART II: Production/Synthesis of Amino Acids

USE OF ENZYMES IN THE SYNTHESIS OF AMINO ACIDS
Introduction
Chemo-Enzymatic Processes to Enantiomerically Pure Amino Acids
Acylase Process
Amidase Process
Hydantoinase Process
Ammonia Lyase Processes
Aminotransferase Process
AADH Process
BETA-AMINO ACID BIOSYNTHESIS
Introduction
Biosynthesis of Beta-Amino Acids
Conclusions and Future Prospects
METHODS FOR THE CHEMICAL SYNTHESIS OF NONCODED ALPHA-AMINO ACIDS FOUND IN NATURAL PRODUCT PEPTIDES
Introduction
Noncoded CAAs
Noncoded Amino Acids by Chemical Modification of Coded Amino Acids
Noncoded Amino Acids with Elaborate Side-Chains
SYNTHESIS OF N-ALKYL AMINO ACIDS
Introduction
N-Methylation via Alkylation
N-Methylation via Schiff?s Base Reduction
N-Methylation by Novel Methods
N-Alkylation of Amino Acids
RECENT DEVELOPMENTS IN THE SYNTHESIS OF BETA-AMINO ACIDS
Introduction
Synthesis of Beta-Amino Acids by Homologation of Alpha-Amino Acids
Chiral Pool: Enantioselective Synthesis of Beta-Amino Acids from Aspartic Acid, Asparagine, and Derivatives
Synthesis of Beta-Amino Acids by Conjugate Addition of Nitrogen Nucleophiles to Enones
Synthesis of Beta-Amino Acids via 1,3-Dipolar Cycloaddition
Synthesis of Beta-Amino Acids by Nucleophilic Additions
Synthesis of Beta-Amino Acids by Diverse Addition or Substitution Reactions
Synthesis of Beta-Amino Acids by Stereoselective Hydrogenation of Prochiral 3-Aminoacrylates and Derivatives
Synthesis of Beta-Amino Acids by Use of Chiral Auxiliaries: Stereoselective Alkylation
Synthesis of Beta-Amino Acids via Radical Reactions
Miscellaneous Methods for the Synthesis of Beta-Amino Acids
Experimental Procedures
SYNTHESIS OF CARBOCYCLIC BETA-AMINO ACIDS
Introduction
Synthesis of Carbocyclic Beta-Amino Acids
Synthesis of Functionalized Carbocyclic Beta-Amino Acid Derivatives
Enzymatic Routes to Carbocyclic Beta-Amino Acids
Experimental Procedures
SYNTHETIC APPROACHES TO ALPHA, BETA-DIAMINO ACIDS
Introduction
Construction of the Carbon Backbone
Introduction of the Nitrogen Atoms in the Carbon Backbone
Experimental Procedures
SYNTHESIS OF HALOGENATED ALPHA-AMINO ACIDS
Introduction
Halogenated Amino Acids with a Hydrocarbon Side-Chain
Halogenated Amino Acids with an Aromatic Side-Chain
Halogenated Amino Acids with Heteroatoms in the Aliphatic Side-Chain
SYNTHESIS OF ISOTOPICALLY LABELED ALPHA-AMINO ACIDS
Introduction
Enzyme-Catalyzed Methods
Chiral Pool Approach
Chemical Asymmetric Methods
Experimental Procedures
SYNTHESIS OF UNNATURAL/NONPROTEINOGENIC ALPHA-AMINO ACIDS
Introduction
Chemical Methods
Enzymatic Methods
Experimental Procedures
SYNTHESIS OF GAMMA AND DELTA-AMINO ACIDS
Introduction
Gamma-Amino Acids
Delta-Amino Acids
SYNTHESIS OF GAMMA-AMINOBUTYRIC ACID ANALOG
Introduction
Alpha-Substituted Gamma-Amino Acids
Beta-Substituted Gamma-Amino Acids
Trisubstituted Gamma-Amino Acids
Hydroxy-Gamma-Amino Acids
Unsaturated Gamma-Amino Acids
Cyclic Gamma-Amino Acids
Experimental Procedures

"The presentation of selected typical experimental procedures is very welcome ... .Provides concise information from the point of view of experts working in the fields, and critically selecting the important recent literature." ( ChemBioChem , March 2010)