Heterocyclic oligoamides as new peptide mimetics [Elektronische Ressource] / vorgelegt von Stefan Miltschitzky
172 Pages
English

Heterocyclic oligoamides as new peptide mimetics [Elektronische Ressource] / vorgelegt von Stefan Miltschitzky

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HETEROCYCLIC OLIGOAMIDES AS NEW PEPTIDE MIMETICS Dissertation zur Erlangung des Grades Doktor der Naturwissenschaften (Dr. rer. nat.) der Naturwissenschaftlichen Fakultät IV Chemie und Pharmazie der Universität Regensburg vorgelegt von Stefan Miltschitzky aus Burghausen 2005 Heterocyclic Oligoamides as New Peptide Mimetics Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) an der Fakultät für Chemie und Pharmazie der Universität Regensburg vorgelegt von Stefan Miltschitzky aus Burghausen 2005 The experimental part of this work was carried out between November 2001 and June 2005 at the Institute for Organic Chemistry at the University of Regensburg under the supervision of Prof. Dr. B. König. The PhD thesis was submitted on: 11.07.2005 The colloquium took place on: 29.07.2005 Board of Examiners: Prof. Dr. G. Schmeer (Chairman) Prof. Dr. B. König (1st Referee) O. Reiser (2nd Fr. Prof. Dr. C. Steinem (Examiner) Meinen Eltern und meiner Familie Table of Contents A. Introduction 1 1. Introduction 1 2. Stabilized α-Peptides with a β-Hairpin Structure and their Biological Application 4 3. Turn Mimics for Peptide Hairpin Structures 13 4. Peptide Hairpin Structure Mimetics 24 5.

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Published 01 January 2006
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HETEROCYCLIC OLIGOAMIDES AS
NEW PEPTIDE MIMETICS





Dissertation
zur Erlangung des Grades

Doktor der Naturwissenschaften (Dr. rer. nat.)

der Naturwissenschaftlichen Fakultät IV
Chemie und Pharmazie
der Universität Regensburg





vorgelegt von
Stefan Miltschitzky
aus Burghausen


2005 Heterocyclic Oligoamides as New
Peptide Mimetics


Dissertation
zur Erlangung des Doktorgrades der Naturwissenschaften
(Dr. rer. nat.)
an der Fakultät für Chemie und Pharmazie
der Universität Regensburg





vorgelegt von
Stefan Miltschitzky
aus Burghausen
2005 The experimental part of this work was carried out between November 2001 and June
2005 at the Institute for Organic Chemistry at the University of Regensburg under the
supervision of Prof. Dr. B. König.





















The PhD thesis was submitted on: 11.07.2005

The colloquium took place on: 29.07.2005

Board of Examiners: Prof. Dr. G. Schmeer (Chairman)
Prof. Dr. B. König (1st Referee) O. Reiser (2nd
Fr. Prof. Dr. C. Steinem (Examiner)





















Meinen Eltern

und meiner Familie
Table of Contents


A. Introduction 1

1. Introduction 1
2. Stabilized α-Peptides with a β-Hairpin Structure and their Biological
Application 4
3. Turn Mimics for Peptide Hairpin Structures 13
4. Peptide Hairpin Structure Mimetics 24
5. Conclusions 34
6. References 35

B. Main Part 43

1. Synthesis of Substituted Pyrimidine Hydrazine Acids (PHA) and
their Use in Peptide Recognition 43
1.1. Introduction 43
1.2. Results and Discussion 45
1.3. Conclusions 60
1.4. Experimental Part 61
1.5. References and Notes 87

2. Substituted Pyrimidine Hydrazine Acid (PHA) Oligoamides and
their Binding Affinity to Peptides and Proteins 89
2.1. Introduction 89
2.2. Synthesis of Highly Water Soluble PHA Receptors 91
2.3. Spectroscopic Investigations of the Substituted PHA Receptors 94
2.4. Binding Affinities of PHA Receptors to Tetradecapeptide
Somatostatin (SRIF) in Different Solvents 98
2.5. Binding Affinities of PHA Receptors to Concanavalin A under
Physiological Conditions 103 2.6. Conclusions 110
2.7. Experimental Part 111
2.8. References 120

3. Molecular Recognition of His with NTA Ligands 123
3.1. Introduction 123
3.2. Results and Discussion 125
3.3. Conclusions 130
3.4. Experimental Part 131
3.5. References and Notes 136

4. Synthesis of an Amino Acid with Protected Cyclen Side Chain
Functionality 139
4.1. Introduction
4.2. Results and Discussion 140
4.3. Conclusions 141
4.4. Experimental Part 143
4.5. References and Notes 147

C. Summary 149

D. Abbreviations 151

E. Appendix 153

F. Acknowledgements 157