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Application of Proteases for the Total Enzymatic Synthesis of the
Cholecystokinin Octapeptide (CCK-8) using Benzoyl-Arginine as
an Enzymatically Cleavable N-Terminal Protecting Group


Anwendung von Proteinen für die vollenzymatische Synthese des
Cholecystokininoctapeptids (CCK-8) unter Verwendung von
Benzoylarginin als enzymatisch spaltbare N-terminale
Schutzgruppe


DISSERTATION

der Fakultät für Chemie und Pharmazie
der Eberhard-Karls-Universität Tübingen

zur Erlangung des Grades eines Doktors
der Naturwissenschaften



2007

vorgelegt von

Rajendra Joshi





























Gedruckt mit Unterstützung des Deutschen Akademischen Austauschdienstes
Application of Proteases for the Total Enzymatic Synthesis of the
Cholecystokinin Octapeptide (CCK-8) using Benzoyl-Arginine as
an Enzymatically Cleavable N-Terminal Protecting Group


Anwendung von Proteinen für die vollenzymatische Synthese des
Cholecystokininoctapeptids (CCK-8) unter Verwendung von
Benzoylarginin als enzymatisch spaltbare N-terminale
Schutzgruppe


DISSERTATION

der Fakultät für Chemie und Pharmazie
der Eberhard-Karls-Universität Tübingen

zur Erlangung des Grades eines Doktors
der Naturwissenschaften



2007

vorgelegt von

Rajendra Joshi


























Tag der mündlichen Prüfung 04.04.2007
Dekan: Prof. Dr. Lars Wesemann
1. Berichterstatter: Prof. Dr. Heiner Eckstein
2. Prof. Dr. Günter Häfelinger
This scientific research work was carried out from April 2004 to January 2007 at the
Institute of Organic Chemistry, Faculty of Chemistry and Pharmacy, Eberhard-Karls-
Universität, Tübingen, Germany, under the guidance of Prof. Dr. Heiner Eckstein.

I would like to express my sincere thanks to Prof. Dr. Heiner Eckstein for his excellent
guidance during my Ph. D. period in Tübingen. Special appreciation is expressed for his
permanent help, generous advices and constructive feedbacks.

A special debt of thanks is due to Prof. Dr. Günter Häfelinger, who critically evaluated
the entire thesis and made several useful suggestions, which have been incorporated here.

I would like to acknowledge the financial support provided by DAAD (Deutscher
Akademischer Austausch Dienst), without which this thesis would not have been a
reality. I thank DAAD for providing me an opportunity not only to achieve my academic
goal but also for giving me a chance to experience German culture and history.
I thank Dr. Liping Meng for helpful discussions and advices, Mrs. Margit Wizemann for
her valuable technical assistance. Special thanks goes to Mr. H. Bartholomä, Mr. R.
Müller and Mr. G. Nicholson for the MS measurements. Similarly Mr. Anurag Mishra
and Ms. Deepti Jha equally deserve acknowledgement for their help during the use of the
LC-ESIMS at the Max Planck Institute, Tübingen.
Last but not least, I would like to acknowledge and mention with sincere gratitude the
efforts and encouragement made by my family members. I thank my wife Sunita for the
correction of typing errors during the preparation of manuscript. I also thank my son
Devansh for not disturbing me while putting things together.






























To My Parents and Family