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Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
2002 In: New Journal of Chemistry, Vol. 26, 834-843 p.Article in journal (Refereed) Published
Place, publisher, year, edition, pages
2002. Vol. 26, 834-843 p.
URN: urn:nbn:se:uu:diva-91465OAI: oai:DiVA.org:uu-91465DiVA: diva2:164202
Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
In thesis
1. Towards the Development of Photoswitchable β-Hairpin Mimetics
Open this publication in new window or tab >>Towards the Development of Photoswitchable β-Hairpin Mimetics
2004 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Peptide secondary structure mimetics are important tools in medicinal chemistry, as they provide analogues of endogeneous peptides with new physicochemical and pharmacological properties. The β-hairpin motif has been shown to be involved in numerous physiological processes, among others in regulation of eucariotic gene transcription. This thesis addresses the design, synthesis and conformational analysis of photoswitchable β-hairpin mimetics.

The developmental work included the establishment of an improved procedure for cross coupling of aryl halides with terminal alkynes. Microwave mediated Sonogashira couplings in closed vessels were optimized under homogeneous and solid-phase conditions furnishing excellent yields for a large variety of substrates within 5 – 25 minutes. In addition, microwave heating was shown not to have any non-conventional effect on the reaction rate.

Furthermore, the most important factors affecting β-hairpin stability were evaluated. Studies of tetrapeptide and decapeptide analogues revealed the essential role of the β-turn in initiation of hairpin folding. Moreover, hydrogen bonding was shown to be the main interchain stabilizing force, whereas hydrophobic interactions were found to be relatively weak. Nevertheless, hydrophobic packing appears to provide an important contribution to the thermodynamic stability of β-hairpins.

Photoswitchable peptidomimetics were prepared by incorporation of various stilbene moieties into tetra- and decapeptides. Synthesis, photochemical isomerisation and spectroscopic conformational analysis of the compounds were performed.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2004. 90 p.
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 950
Organic chemistry, β-hairpin, peptidomimetics, Sonogashira, NMR, photochemistry, microwave, peptide, palladium, Organisk kemi
National Category
Organic Chemistry
urn:nbn:se:uu:diva-4057 (URN)91-554-5897-1 (ISBN)
Public defence
2004-04-02, B41, BMC, Husargatan 3, 751 23 Uppsala, 10:15
Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved

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