Coordinative peptide recognition [Elektronische Ressource] : making intermolecular processes intramolecular / vorgelegt von Michael Kruppa
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Coordinative peptide recognition [Elektronische Ressource] : making intermolecular processes intramolecular / vorgelegt von Michael Kruppa

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Published 01 January 2006
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COORDINATIVE PEPTIDE RECOGNITION

Making Intermolecular Processes Intramolecular










Dissertation

Zur Erlangung des Doktorgrades der Naturwissenschaften
(Dr. rer. nat.)
der naturwissenschaftlichen Fakultät IV
– Chemie und Pharmazie –
der Universität Regensburg















vorgelegt von
Michael Kruppa
aus Erlangen

2005 Coordinative Peptide Recognition

Making Intermolecular Processes Intramolecular






Dissertation
Zur Erlangung des Doktorgrades der Naturwissenschaften
(Dr. rer. nat.)
der naturwissenschaftlichen Fakultät IV
– Chemie und Pharmazie –
der Universität Regensburg










vorgelegt von
Michael Kruppa
aus Erlangen

2005 The experimental part of this work was carried out between October 2002 and April
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: 31.05.2005

The colloqium took place on: 24.06.2005

Board of Examiners: Prof. Dr. R. Gschwind (Chairman)
Prof. Dr. B. König (1st Referee)
O. Reiser (2nd
Dr. A. Pfitzner (Examiner)
















Für meine geliebten Eltern

Acknowledgements

I would like to express my sincere gratitude to Prof. Dr. B. König, for his continued
guidance, advice and encouragement throughout this work.

Thanks are extended to the analytical departments of the University of Regensburg for
the prompt and accurate measurement of my numerous, often difficult samples. Special
thanks to Dr. T. Burgemeister, Mr. F. Kastner, Ms. N. Pustet, Ms. A. Schramm and Ms.
G. Stühler (NMR), Dr. K. K. Mayer, Mr. J. Kiermaier and Mr. W. Söllner (MS), Mr. G.
Wandinger, Ms. S. Stempfhuber and Mr. H. Schüller (elemental analysis), Dr. M. Zabel
(X-ray crystallography) and Dr. R. Vasold (HPLC).

My special thanks go to:
All colleagues, past and present at the University of Regensburg, for making the
working environment positive, constructive, as well as relaxed.

Daniel Vomasta, Andreas Grauer and Nicole Holub for their efforts during their
research period in my laboratory.

Daniel Frank for his work during his Zulassungsarbeit.

Mrs. Helga Leffler-Schuster for the potentiometric titrations and here marvellous
reports about foreign countries.

Dr. Thomas Walenzyk, Daniel Vomasta, Eva Engel, Michael Egger and Stefan Ritter
for their corrections of this work.

Dr. Maria Teresa Hechavarria Fonseca and Thomas Suhs for the fabulous time in
laboratory.

My very special thanks go to:
Stefan Ritter for the wonderful time in China, the very delicious dinners and his
infectious laughter.
Eva Engel for all the tasty cakes and sweets. Thanks also for the time at Tai-Bo lessons
and all the climbing trips to Schönhofen.

Stefan Miltschitzky for his fabulous cooking and the perfect time in Italy. Thank you for
your tireless microcalorimetrical titrations.

Giovanni Imperato for making live better since he appeared in our working group.
Thanks Gio for all your Italian dishes and showing me how to climb up mountains.
Thank you also for one unforgettable weak in my life staying in Italy.

Dr. Christian Mandl and Dr. Christoph Bonauer for cooperation in two great projects
and all the great ideas. Thank you also for all the private discussions until the early
mornings. I am not able to say how much they influenced my life.

Dr. Thomas Walenzyk for showing up in my live. Thanks Thomas for all the evenings,
discussions, and support in any situations of my life.

Christian Geiger for three wonderful years in our apartment.

Doris Huber for showing me that there is still a lot more in life than chemistry and
working. Thanks for your patience and your love.

My parents for all their support and love. Content
Page
A. Introduction 1
1. Iminodiacetato (IDA) Complexes 4
2. Nitrilotriacetato (NTA) Complexes 36
3. Bis-(2-pyridylmethyl)-amine (BPA) Complexes 61
4. Tris-(2-pyridylmethyl)-amine (TPA) Complexes 87
B. Main Part 117
1. Investigation of Metal Complex – Amino Acid Side
Chain Interactions by Potentiometric Titration 117
1.1 Introduction 118
1.2 Results and Discussion 120
1.3 Conclusion 129
1.4 Experimental Section 131
2. Molecular Recognition using Modular Receptor Synthesis 137
2.1 Terminal Receptor Building Blocks 139
2.1.1 N-terminal Receptor Building Blocks 139
2.1.2 C-terminal Receptor Building Blocks 143
2.1.3 Terminal Recognition Units with two Chelating Sites 148
2.1.4 SPRS (Solid Phase Receptor Synthesis) 152
2.2 Receptors as Side Chains of Amino Acids 156
2.2.1 Tyrosine based Receptor 156
2.2.2 Phenylalanine based Receptors 157
2.3 Conclusion 160
2.4 Experimental Section 163
3. Enhanced Peptide b-Sheet Affinity by Metal to Ligand Coordination 202
3.1 Introduction 203
3.2 Results and Discussion 204
3.3 Conclusion 208
3.4 Experimental Section 211 4. A Luminescent Receptor with Imidazole and Ammonium
Ion Affinity for Peptide Binding in Aqueous Solution 224
4.1 Introduction 225
4.2 Results and Discussion 225
4.3 Conclusion 231
4.4 Experimental Section 234
5. Receptor for Protein Surfaces with Affinity to Histidine
and phosphorylated Amino Acids 242
5.1 Experimental Section 244
C. Appendix 247