The Amide Linkage Structural Significance in Chemistry, Biochemistry, and Materials Science

by Greenberg, Arthur; Breneman, Curt M.; Liebman, Joel F.

• ISBN13: 9780471358930
• ISBN10: 0471358932
• Edition: 1st
• Format: Hardcover
• Copyright: 2000-01-04
• Publisher: Wiley-Interscience

Summary

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.

Author Biography

ARTHUR GREENBERG, PhD, is Professor in the Department of Chemistry at the University of New Hampshire.

CURT M. BRENEMAN, PhD, is Professor in the Department of Chemistry at Rensselaer Polytechnic Institute.

JOEL F. LIEBMAN, PhD, is Professor in the Department of Chemistry and Biochemistry at the University of Maryland, Baltimore County.

Table of Contents

Preface	ix
Contributors	xi
The Electron Density Distribution of Amides and Related Compounds	1	(32)
Curt M. Breneman
Martin Martinov
Origin of the Amide Rotational Barrier	33	(14)
Kenneth B. Wiberg
The Amide Linkage as a Ligand---lts Properties and the Role of Distortion	47	(38)
Arthur Greenberg
Studies in Amide Hydrolysis: The Acid, Base, and Water Reactions	85	(30)
Robert S. Brown
The Thermochemistry of Amides	115	(22)
Joel F. Liebman
Hussein Y. Afeefy
Suzanne W. Slayden
Stereospecificity in the α-Lactam (Aziridinone) Synthon	137	(20)
Robert V. Hoffman
β-Lactams: Cyclic Amides of Distinction	157	(58)
Ajay K. Bose
Maghar S. Manhas
Bimal K. Banik
Vaidyanathan Srirajan
Sterically Hindered Twisted Amides	215	(32)
Shinji Yamada
Photoelectron Spectroscopy of Amides and Lactams	247	(44)
Paul Rademacher
The Role of Amides in the Noncovalent Synthesis of Supramolecular Structures in Solution, at Interfaces, and in Solids	291	(46)
G. Tayhas R. Palmore
John C. MacDonald
β-Lactam Antibacterial Agents: Computational Chemistry Investigations	337	(40)
Donald B. Boyd
Three-Dimensional Design of Enzyme Inhibitors with Heterocyclic Amide Bond Mimics	377	(32)
Regine S. Bohacek
William C. Shakespeare
Ab Initio conformational Analysis of Protein subunits: A Case Study of the Serine Diamide Model	409	(54)
Andras Perczel
Imre G. Csizmadia
Gas-Phase Ion Chemistry of Amides, Peptides, and Proteins	463	(32)
Carolyn J. Cassady
β-Sheet Interactions between Proteins	495	(24)
Santanu Maitra
James S. Nowick
Head-to-Tail Cyclic Peptides and Cyclic Peptide Libraries	519	(46)
Arno F. Spatola
Peteris Romanovskis
From Crystaly Structures of Oligopeptides to Protein Folding: The Importance of Peptide Bond---Side chain Hyperconjugation	565	(34)
Andrzej S. Cieplak
Role of the Peptide Bond in Protein Structure and Folding	599	(28)
Neville R. Kallenbach
Anthony J. Bell, Jr.
Erik J. Spek
Index	627