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Towards the Development of Photoswitchable β-Hairpin Mimetics
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Kemiska institutionen, Avdelningen för organisk kemi.
2004 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Uppsala: Acta Universitatis Upsaliensis , 2004. , s. 90
Serie
Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1104-232X ; 950
Emneord [en]
Organic chemistry, β-hairpin, peptidomimetics, Sonogashira, NMR, photochemistry, microwave, peptide, palladium
Emneord [sv]
Organisk kemi
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-4057ISBN: 91-554-5897-1 (tryckt)OAI: oai:DiVA.org:uu-4057DiVA, id: diva2:164205
Disputas
2004-04-02, B41, BMC, Husargatan 3, 751 23 Uppsala, 10:15
Opponent
Veileder
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
Delarbeid
1. Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating
Åpne denne publikasjonen i ny fane eller vindu >>Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating
2001 Inngår i: Journal of Organic Chemistry, Vol. 66, nr 12, s. 4165-4169Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:uu:diva-91463 (URN)
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
2. Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase
Åpne denne publikasjonen i ny fane eller vindu >>Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase
2003 (engelsk)Inngår i: Journal of Organic Chemistry, Vol. 68, nr 16, s. 6431-6434Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

A microwave-enhanced, rapid, and efficient solidphase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15 to 25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

HSV kategori
Identifikatorer
urn:nbn:se:uu:diva-91464 (URN)10.1021/jo034284s (DOI)
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11 Sist oppdatert: 2011-01-05
3. Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics
Åpne denne publikasjonen i ny fane eller vindu >>Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics
2002 Inngår i: New Journal of Chemistry, Vol. 26, s. 834-843Artikkel i tidsskrift (Fagfellevurdert) Published
Identifikatorer
urn:nbn:se:uu:diva-91465 (URN)
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
4. Synthesis and Conformational Analysis of Novel Stibene-type Peptidomimetics
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis and Conformational Analysis of Novel Stibene-type Peptidomimetics
Vise andre…
Artikkel i tidsskrift (Fagfellevurdert) Submitted
Identifikatorer
urn:nbn:se:uu:diva-91466 (URN)
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert
5. Synthesis and Conformational Analysis of Novel β-Hairpin mimetics. Factors Affecting Stability and Incorporation of a Photoswitchable Dipeptide Mimic
Åpne denne publikasjonen i ny fane eller vindu >>Synthesis and Conformational Analysis of Novel β-Hairpin mimetics. Factors Affecting Stability and Incorporation of a Photoswitchable Dipeptide Mimic
Artikkel i tidsskrift (Fagfellevurdert) Submitted
Identifikatorer
urn:nbn:se:uu:diva-91467 (URN)
Tilgjengelig fra: 2004-03-11 Laget: 2004-03-11bibliografisk kontrollert

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