Abstract
Transannular hydrogen bonding stabilizes a left-handed double helical conformation in the tryptophan-derived tetraazacyclooctadecane 1 both in solution and the solid state, whereas the analogous tryptamine-derived macrocycle 2 shows less tendency towards intramolecular hydrogen bonding and does not exist as a helix in the crystal. Azamacrocycles 1 and 2 are synthesized by a novel method and their secondary structure analysed by NMR spectroscopy, circular dichroism and X-ray diffraction. Molecular modelling does not account for the conformational differences between 1 and 2.
Original language | English (US) |
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Pages (from-to) | 2427-2433 |
Number of pages | 7 |
Journal | Journal of the Chemical Society - Perkin Transactions 1 |
Issue number | 20 |
State | Published - 1996 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry