The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science / Edition 1

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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.

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Editorial Reviews

From the Publisher
"It makes extremely interesting reading" (Angewandte Chemie, International Edition 19 November 2001)

"...will have a longer than average shelf life..."(European Peptide Society Newsletter, 1 January 2003)

"...excellent chapters and provides plenty of useful background information on amide structure." (Angewandte Chemie, International Edition, Vol. 42, 2003)

Meant to complement Zabicky's 1970 by being broader in scope and placing less emphasis on the synthesis and reactions of amides, the 18 studies present many aspects of the structure, bonding, and dynamics of amides and their influences on chemical, physical, biological, and material properties. They focus on structural, energetics, and bonding perspective with a view to understanding physical and chemical properties. They also provide background and context for non-experts before sounding the depths in a particular area. Their topics include the electron density distribution of amides and related compounds, the properties and the role of distortion of the amide linkage as a ligand, the thermochemistry, beta-lactams as cyclic amides of distinction, sterically hindered twisted amides, the three-dimensional design of enzyme inhibitors with heterocyclic amide bond mimics, head-to-tail cyclic peptides and cyclic peptide libraries, and the role of the peptide bond in protein structure and folding. The subtitle on the cover differs from other versions by reading Structural Significance in Chemistry, Biochemistry, and Materials Science. Annotation c. Book News, Inc., Portland, OR (
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Product Details

  • ISBN-13: 9780471358930
  • Publisher: Wiley
  • Publication date: 1/28/2000
  • Edition description: New Edition
  • Edition number: 1
  • Pages: 672
  • Product dimensions: 6.38 (w) x 9.65 (h) x 1.48 (d)

Meet the Author

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.

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Table of Contents

1 The Electron Density Distribution of Amides and Related Compounds 1
2 Origin of the Amide Rotational Barrier 33
3 The Amide Linkage as a Ligand - Its Properties and the Role of Distortion 47
4 Studies in Amide Hydrolysis: The Acid, Base, and Water Reactions 85
5 The Thermochemistry of Amides 115
6 Stereospecificity in the [alpha]-Lactam (Aziridinone) Synthon 137
7 [beta]-Lactams: Cyclic Amides of Distinction 157
8 Sterically Hindered Twisted Amides 215
9 Photoelectron Spectroscopy of Amides and Lactams 247
10 The Role of Amides in the Noncovalent Synthesis of Supramolecular Structures in Solution, at Interfaces, and in Solids 291
11 [beta]-Lactam Antibacterial Agents: Computational Chemistry Investigations 337
12 Three-Dimensional Design of Enzyme Inhibitors with Heterocyclic Amide Bond Mimics 377
13 Ab Initio Conformational Analysis of Protein Subunits: A Case Study of the Serine Diamide Model 409
14 Gas-Phase Ion Chemistry of Amides, Peptides, and Proteins 463
15 [beta]-Sheet Interactions Between Proteins 495
16 Head-to-Tall Cyclic Peptides and Cyclic Peptide Libraries 519
17 From Crystal Structures of Oligopeptides to Protein Folding: The Importance of Peptide Bond-Side Chain Hyperconjugation 565
18 Role of the Peptide Bond in Protein Structure and Folding 599
Index 627
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