Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles

Mark Mascal, Ian G. Wood, Michael J. Begley, Andre S. Batsanov, Timothy Walsgrove, Alexandra M Z Slawin, David J. Williams, Alex F. Drake, Giuliano Siligardi

Research output: Contribution to journalArticle

12 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2427-2433
Number of pages7
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number20
StatePublished - 1996
Externally publishedYes

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Hydrogen bonds
Molecular modeling
Tryptophan
Nuclear magnetic resonance spectroscopy
Conformations
X ray diffraction
Crystals
indole
tryptamine

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., ... Siligardi, G. (1996). Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles. Journal of the Chemical Society - Perkin Transactions 1, (20), 2427-2433.

Indole-fused tetraazacyclooctadecanes : Double-helical macrocycles. / Mascal, Mark; Wood, Ian G.; Begley, Michael J.; Batsanov, Andre S.; Walsgrove, Timothy; Slawin, Alexandra M Z; Williams, David J.; Drake, Alex F.; Siligardi, Giuliano.

In: Journal of the Chemical Society - Perkin Transactions 1, No. 20, 1996, p. 2427-2433.

Research output: Contribution to journalArticle

Mascal, M, Wood, IG, Begley, MJ, Batsanov, AS, Walsgrove, T, Slawin, AMZ, Williams, DJ, Drake, AF & Siligardi, G 1996, 'Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles', Journal of the Chemical Society - Perkin Transactions 1, no. 20, pp. 2427-2433.
Mascal M, Wood IG, Begley MJ, Batsanov AS, Walsgrove T, Slawin AMZ et al. Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles. Journal of the Chemical Society - Perkin Transactions 1. 1996;(20):2427-2433.
Mascal, Mark ; Wood, Ian G. ; Begley, Michael J. ; Batsanov, Andre S. ; Walsgrove, Timothy ; Slawin, Alexandra M Z ; Williams, David J. ; Drake, Alex F. ; Siligardi, Giuliano. / Indole-fused tetraazacyclooctadecanes : Double-helical macrocycles. In: Journal of the Chemical Society - Perkin Transactions 1. 1996 ; No. 20. pp. 2427-2433.
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