Issue 7, 2002
From the journal:

New Journal of Chemistry

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

Máté Erdélyi,ab   Vratislav Langer,c   Anders Karlénb  and  Adolf Gogoll*a  

* Corresponding authors

a Department of Organic Chemistry, Uppsala University, Box 531, Uppsala, Sweden
E-mail: adolf@kemi.uu.se
Fax: +46 18 512 524

b Department of Medicinal Chemistry, Uppsala University, Box 574, Uppsala, Sweden
Fax: +46 18 471 4474

c Department of Environmental Inorganic Chemistry, Chalmers University of Technology, Göteborg, Sweden
Fax: +46 31 772 2853

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B111241D
Article type
Paper
Submitted
10 Dec 2001
Accepted
23 Apr 2002
First published
06 Jun 2002

New J. Chem., 2002,26, 834-843

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

M. Erdélyi, V. Langer, A. Karlén and A. Gogoll, New J. Chem., 2002, 26, 834 DOI: 10.1039/B111241D

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