473932-28-4Relevant articles and documents
Insight into β-hairpin stability: A structural and thermodynamic study of diastereomeric β-hairpin mimeticsy
Erdelyi, Mate,Langer, Vratislav,Karlen, Anders,Gogoll, Adolf
, p. 834 - 843 (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.