Insight into beta-hairpin stability: a structural and thermodynamic study of diastereomeric beta-hairpin mimetics
2002 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 26, 834-843 p.Article in journal (Refereed) Published
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.
Medical and Health Sciences
IdentifiersURN: urn:nbn:se:uu:diva-64334DOI: 10.1039/B111241DOAI: oai:DiVA.org:uu-64334DiVA: diva2:92245