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 journalArticlepeer-review

12 Scopus citations


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

ASJC Scopus subject areas

  • Organic Chemistry


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