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Insight into beta-hairpin stability: a structural and thermodynamic study of diastereomeric beta-hairpin mimetics
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. (Organic Pharmaceutical Chemistry)
Department of Environmental Inorganic Chemistry, Chalmers University of Technology.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. (Organic Pharmaceutical Chemistry)
2002 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 26, 834-843 p.Article in journal (Refereed) Published
Abstract [en]

Two diastereomers of a model β-hairpin peptide mimetic were synthesized and studied with a combination of experimental (NMR, X-ray, CD, MS, IR) and computational methods (Monte Carlo/molecular mechanics calculations). The secondary structure-stabilizing effects of hydrophobic interactions and hydrogen bonding were investigated. Comparison of the extent of folded hairpin population in non-competitive, polar aprotic, and polar protic solvents illustrates the critical role of intramolecular hydrogen bonding on hairpin stability. Investigation of 1H NMR melting curves of the diastereomeric compounds in a variety of solvents allowed an evaluation of the role of hydrophobic effects on secondary structure stabilization to be made.

Place, publisher, year, edition, pages
2002. Vol. 26, 834-843 p.
National Category
Medical and Health Sciences
Identifiers
URN: urn:nbn:se:uu:diva-64334DOI: 10.1039/B111241DOAI: oai:DiVA.org:uu-64334DiVA: diva2:92245
Available from: 2008-10-17 Created: 2008-10-17 Last updated: 2017-11-30Bibliographically approved

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Gogoll, Adolf

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