Amino Acids, Peptides and Proteins in Organic Chemistry

PART I: Synthesis and Chemistry of Modified Amino Acids

SYNTHESIS AND CHEMISTRY OF ALPHA, BETA-DIDEHYDROAMINO ACIDS
Introduction
Synthesis of DDAAs
Reactions of DDAAs
Experimental Procedures
SYNTHESIS AND CHEMISTRY OF ALPHA-HYDRAZINO ACIDS
Introduction
Synthesis
Chemistry
Experimental Procedures
HYDROXAMIC ACIDS: CHEMISTRY, BIOACTIVITY, AND SOLUTION- AND SOLID-PHASE SYNTHESIS
Introduction
Chemistry, Bioactivity, and Clinical Utility
Solution-Phase Synthesis of Hydroxamic Acids
Solid-Phase Synthesis of Hydroxamic Acids
Experimental Procedures
CHEMISTRY OF ALPHA-AMINOBORONIC ACIDS AND THEIR DERIVATIVES
Introduction
Synthesis of Alpha-Aminoboronic Acids
Synthesis of Alpha-Aminoboronic Acid Derivatives
Asymmetric Synthesis via Alpha-Haloalkylboronic Esters
Synthesis of Glycine Alpha-Aminoboronic Acids
Synthesis of Proline Alpha-Aminoboronic Acids
Synthesis of Alanine Alpha-Aminoboronic Acids
Synthesis of Ornithine Alpha-Aminoboronic Acids
Synthesis of Arginine Alpha-Aminoboronic Acids
Synthesis of Phenethyl Peptide Boronic Acids
Synthesis via Zirconocene Species
Synthesis and Activity of Amine-Carboxyboranes and their Derivatives
Synthesis of Boron Analogs of Phosphonoacetates
CHEMISTRY OF AMINOPHOSPHONIC ACIDS AND PHOSPHONOPEPTIDES
Introduction
Physical/Chemical Properties and Analysis
Synthesis of Alpha-Aminophosphonic Acids
Synthesis of Beta-Aminophosphonates
Synthesis of Gamma-Aminophosphonates and Higher Homologs
Phosphono- and Phosphinopeptides
Remarks on the Practical Utility of Aminophosphonates
Experimental Procedures
CHEMISTRY OF SILICON-CONTAINING AMINO ACIDS
Introduction
Synthesis of Silicon-Containing Amino Acids
Reactions of Silicon-Containing Amino Acids
Bioactive Peptides Incorporating Silicon-Substituted Amino Acids
Experimental Procedures

PART II: Amino Acid Organocatalysis

CATALYSIS OF REACTIONS BY AMINO ACIDS
Introduction
Aldol Reaction
Mannich Reaction
Alpha-Amination Reaction
Michael Reaction
Morita-Baylis-Hillman Reactions and their Aza Counterpart
Miscellaneous Amino Acid-Catalyzed Reactions
Sustainability of Amino Acid Catalysis
Experimental Procedures

PART III: Enzymes

PROTEASES AS POWERFUL CATALYSTS FOR ORGANIC SYNTHESIS
Enzyme Biocatalysis
Proteolytic Enzymes: Mechanisms and Characteristics
Proteases as Process Catalysts
Proteases in Organic Synthesis
Peptide Synthesis
SEMISYNTHETIC ENZYMES
Usefulness of Semisynthetic Enzymes
Natural Protein Biosynthesis
Sense Codon Reassignment
Missense Suppression
Evolving the Orthogonal aaRS/tRNA Pair
Nonsense Suppression
Mischarging of rRNA by Ribozyme
Evolving the Orthogonal Ribosome/mRNA Pair
Frame-Shift Suppression
Noncanonical Base Pairs
Chemical Ligation
Inteins
EPL
Post-Transitional Chemical Modification
Examples of Semisynthetic Enzymes
CATALYSIS BY PEPTIDE-BASED ENZYME MODELS
Introduction
Peptide Models of Hydrolytic Enzymes
Peptide Models of Heme Proteins
SUBSTRATE RECOGNITION
Recognition, Specificity, Catalysis, Inhibition, and Linguistics
Serine Proteinases
Cysteine Proteinases
Glycoside Hydrolases
Protein Kinases
aaRSs
Lipases
PROTEIN RECOGNITION
General Introduction
Nature of Protein Interfaces
Affinity of Protein Interactions
Measuring Protein Interactions
Coupled Folding and Binding
Regulation of Interactions by PTMs
Engineering and Inhibiting Protein-Protein Interactions
MAMMALIAN PEPTIDE HORMONES: BIOSYNTHESIS AND INHIBITION
Introduction
Mammalian Peptide Hormones
Biosynthesis of Peptide Hormones
Inhibition of Biosynthesis
INSECT PEPTIDE HORMONES
Introductin
Structure and Biosynthesis of Insect Peptide Hormones
Proctolin
Sex Peptide
A-Type Allatostatins
CRF-Related DHs
Insect Peptide Hormones and Insect Control
PLANT PEPTIDE SIGNALS
Introduction
Defense-Related Peptides
Peptides Involved in Growth and Development
Peptides Involved in Self-Recognition
Methods in Plant Regulatory Peptide Research
NONRIBOSOMAL PEPTIDE SYNTHESIS
Introduction
NRPs
NRP Synthetase Domains
PPTases
Experimental Strategies for NRPS Investigations
Non-NRPs

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.