Properties and Synthesis of Red-Ox Active Proline Mimics Open Access

Shugart, John H. (2008)

Permanent URL: https://etd.library.emory.edu/concern/etds/sj1392371?locale=en
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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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