Issue 20, 1996

Indole-fused tetraazacyclooctadecanes: double-helical macrocycles

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 2427-2433

Indole-fused tetraazacyclooctadecanes: double-helical macrocycles

M. Mascal, I. G. Wood, M. J. Begley, A. S. Batsanov, T. Walsgrove, A. M. Z. Slawin, D. J. Williams, A. F. Drake and G. Siligardi, J. Chem. Soc., Perkin Trans. 1, 1996, 2427 DOI: 10.1039/P19960002427

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