Paper

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

---

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

Máté Erdélyi, Vratislav Langer, Anders Karlén and Adolf Gogoll

---

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.

About this Journal

• Journal Home
• About the Journal

Read the Journal

• Advance Articles
• Browse Issues
• Search RSC Journals
• RSC Prospect Structure Search
• E-Alerts Service
• RSS feed

ReSourCe

• Submit an Article
• Author Guidelines
• Ethical Guidelines
• Copyright & Permissions
• Referee Report Forms

Explore the Journal

• Hot Articles
• Cover Gallery
• Top 10
• People and Contacts

Customer Services

• Subscriptions
• Advertising
• Librarians

Tools