Properties and Synthesis of Red-Ox Active Proline Mimics 公开
Shugart, John H. (2008)
Published
Abstract
A balance of factors composed of sterics, nonbonded interactions, and stereoelectronics account for the structural preferences seen in individual amino acids, and subsequently in the global structure of peptides and proteins. These factors in the amino acid proline present a method to potentially control macromolecular structure. Thiazolidine-4-carboxylic acid presents a pseudoproline with Red-Ox potential that can be stereoselectively oxidized. In this study the conformational dynamics of the stereoselective oxidation of molecular systems containing thiazolidine-4-carboxylic acid are explored and evaluated for their potential utility as a Red-Ox switch for the self assembly of peptides. Ultimately, it was determined that through stereoselective oxidation the conformational properties of the proline-like thiazolidine-4-carboxylic acid can be modulated to select for different conformational preferences.
Table of Contents
Chapter 1. Introduction
Introduction
Collagen
Model Studies of Proline, 4-Hydroxyproline, and 4-Fluoroproline
C-Oxygen substituted prolines
Polar groups at the C position
C Substituted Compounds
Conclusion
References
Chapter 2. Synthesis, analysis, and crystal structures of epimeric S-oxo-Thiazolidine-(R)-Carboxylic Acid Derivatives
Introduction
Results and Discussion
Synthesis
Confirmation Analysis of X-Ray Structures
Amide Vibrational Modes
Computational Chemistry and NMR Studies
Conclusion
Materials and Methods
X-Ray Crystallography
References
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