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Conformational analysis of 4-azidoproline derivatives and their application in molecular recognition

Sonntag, Louis-Sebastian. Conformational analysis of 4-azidoproline derivatives and their application in molecular recognition. 2005, Doctoral Thesis, University of Basel, Faculty of Science.

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Official URL: http://edoc.unibas.ch/diss/DissB_7201

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Abstract

This thesis presents studies on the influence of 4-azido-substitutents in azidoproline on the
conformation of the pyrrolidine ring system as well as the conformation around the peptide
bond in acetylated monomers and dimers. The azido-group may be reduced to an amine,
which allows for further modifications. The insights gained were applied to the synthesis of a
tripodal molecular scaffold. This scaffold was used as a backbone for a synthetic receptor,
which binds peptides in aqueous solution.
In the first part of this thesis the effect of the azido-substituent on the conformation of
4-azidoproline is described. By NMR-spectroscopy, X-ray diffraction, FT-IR spectroscopy
and ab initio calculations, the conformation of 4-azidoproline derivatives was analyzed.
Particular focus was laid on the s-cis:s-trans ratio and the factors influencing it. Furthermore,
the kinetics of the interconversion of the s-cis and s-trans conformation of diastereomeric
4-azidoproline derivatives were determined by EXSY-NMR.
The second part of this thesis describes the synthesis and structural analysis of the
azido-functionalized cyclotriproline and its application as a molecular scaffold for a peptide
receptor. The binding properties were analyzed in on-bead screenings against an encoded
tripeptide library in different buffer solutions. The binding affinity to a selected peptide was
measured by isothermal titration calorimetry (ITC).
Advisors:Wennemers, Helma
Committee Members:Giese, Bernd and Séquin, Urs Marcel
Faculties and Departments:05 Faculty of Science > Departement Chemie > Former Organization Units Chemistry > Bioorganische Chemie (Wennemers)
UniBasel Contributors:Wennemers, Helma and Giese, Bernd
Item Type:Thesis
Thesis Subtype:Doctoral Thesis
Thesis no:7201
Thesis status:Complete
Bibsysno:Link to catalogue
Number of Pages:111
Language:English
Identification Number:
Last Modified:22 Jan 2018 15:50
Deposited On:13 Feb 2009 15:12

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