Insight into &#946 -hairpin stability: a structural and thermodynamic study of diastereomeric &#946-hairpin mimetics
Journal article, 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.

X-ray

MS

hydrogen bonds

IR

CD

crystal structure

NMR

Author

Máté Erdélyi

Vratislav Langer

Chalmers, Department of Environmental Inorganic Chemistry

Anders Karlén

Adolf Gogoll

New Journal of Chemistry

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

Vol. 26 7 834-843

Subject Categories

Organic Chemistry

More information

Created

10/6/2017