The Amide Linkage

The amide linkage is one of the most fundamental and widespread chemical bonds in nature, underlying the properties of a vast array of organic molecules, polymers, and materials, including peptides and proteins. Arthur Greenberg, Curt Breneman, and Joel Liebman’s peerless text provides comprehensive coverage of the experimental, structural, and computational findings that shed light on the chemical and physical properties of the amide linkage, as well as its emerging applications in materials and biotechnology. Chapters in The Amide Linkage highlight how this chemical bond factors in the design of enzyme inhibitors, cyclic peptides, antibacterial agents, and emerging nanotechnology applications. This one-of-a-kind study also: Discusses selected aspects of chemical reactions, structure, bonding, and energetics of the amide bond, including amide rotational barriers, stereochemistry, complexation, spectroscopy, and thermochemistry Presents specific applications to supramolecular and stereospecific synthesis Discusses ke y aspects of peptide and protein chemistry–such as molecular recognition, conformation, and folding–in terms of the amide linkage Includes chapters contributed by numerous eminent chemists and biochemists Organic, medicinal, polymer, and physical chemists, as well as biochemists and materials scientists, will find The Amide Linkage to be an invaluable addition to their professional libraries.

The Electron Density Distribution of Amides and Related Compounds (C. Breneman & M. Martinov). Origin of the Amide Rotational Barrier (K. Wiberg). The Amide Linkage as a Ligand-Its Properties and the Role of Distortion (A. Greenberg). Studies in Amide Hydrolysis: The Acid, Base, and Water Reactions (R. Brown). The Thermochemistry of Amides (J. Liebman, et al.). Stereospecificity in the -Lactam (Aziridinone) Synthon (R. Hoffman). -Lactams: Cyclic Amides of Distinction (A. Bose, et al.). Sterically Hindered Twisted Amides (S. Yamada). Photoelectron Spectroscopy of Amides and Lactams (P. Rademacher). The Role of Amides in the Noncovalent Synthesis of Supramolecular Structures in Solution, at Interfaces, and in Solids (G. Palmore & J. MacDonald). -Lactam Antibacterial Agents: Computational Chemistry Investigations (D. Boyd). Three-Dimensional Design of Enzyme Inhibitors with Heterocyclic Amide Bond Mimics (R. Bohacek & W. Shakespeare). Ab Initio Conformational Analysis of Protein Subunits: A Case Study of the Serine Diamide Model (A. Perczel & I. Csizmadia). Gas-Phase Ion Chemistry of Amides, Peptides, and Proteins (C. Cassady). -Sheet Interactions Between Proteins (S. Maitra & J. Nowick). Head-to-Tail Cyclic Peptides and Cyclic Peptide Libraries (A. Spatola & P. Romanovskis). From Crystal Structures of Oligopeptides to Protein Folding. The Importance of Peptide Bond-Side Chain Hyperconjugation (A. Cieplak). Role of the Peptide Bond in Protein Structure and Folding (N. Kallenbach, et al.). Index.