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) |
|---|---|
| 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 |
Fingerprint
ASJC Scopus subject areas
- Organic Chemistry
Cite this
Mascal, M., Wood, I. G., Begley, M. J., Batsanov, A. S., Walsgrove, T., Slawin, A. M. Z., Williams, D. J., Drake, A. F., & Siligardi, G. (1996). Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles. Journal of the Chemical Society - Perkin Transactions 1, (20), 2427-2433.