Abstract
Inspired by the topological similarity between ladder-like cyclic ether skeletons and α-helical peptides, a trans-fused 6/6/6/6 tetracyclic ether containing two hydroxyl groups separated by a distance of 4.8 Å was designed as a scaffold for a nonpeptidic α-helix mimetic. Two alkyl guanidinium groups were attached to the hydroxyl groups to develop a synthetic receptor for the specific recognition of i + 4 spaced aspartate pairs on the surface of an α-helical peptide. A circular dichroism (CD) titration showed that this mode of molecular recognition stabilizes α-helical structures of peptides containing i + 4 spaced aspartate pairs.
Original language | English |
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Pages (from-to) | 5801-5805 |
Number of pages | 5 |
Journal | Tetrahedron Letters |
Volume | 47 |
Issue number | 32 |
DOIs | |
Publication status | Published - 2006 Aug 7 |
Keywords
- Molecular recognition
- Polycyclic ether
- Scaffold
- α-Helix mimetic
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry