Paper

New J. Chem., 2002, 26, 834 - 843, DOI: 10.1039/b111241d

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Insight into -hairpin stability: a structural and thermodynamic study of diastereomeric -hairpin mimetics

Máté Erdélyi, Vratislav Langer, Anders Karlén and Adolf Gogoll

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Two diastereomers of a model -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.

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