Insight into &#946 -hairpin stability: a structural and thermodynamic study of diastereomeric &#946-hairpin mimetics
Artikel i vetenskaplig tidskrift, 2002

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.



hydrogen bonds



crystal structure



Máté Erdélyi

Vratislav Langer

Chalmers, Institutionen för oorganisk miljökemi

Anders Karlén

Adolf Gogoll

New Journal of Chemistry

1144-0546 (ISSN) 1369-9261 (eISSN)

Vol. 26 834-843


Organisk kemi