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

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 journal › Article › peer-review

12 Scopus citations

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

ASJC Scopus subject areas

Organic Chemistry

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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 journal › Article › peer-review

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

year = "1996",

language = "English (US)",

pages = "2427--2433",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

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T2 - Double-helical macrocycles

AU - Mascal, Mark

AU - Wood, Ian G.

AU - Begley, Michael J.

AU - Batsanov, Andre S.

AU - Walsgrove, Timothy

AU - Slawin, Alexandra M Z

AU - Williams, David J.

AU - Drake, Alex F.

AU - Siligardi, Giuliano

PY - 1996

Y1 - 1996

N2 - 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.

AB - 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.

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JF - Journal of the Chemical Society. Perkin Transactions 1

SN - 1470-4358

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ER -

Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles

Abstract

ASJC Scopus subject areas

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