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; G  Siligardi

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, G Siligardi

Research output: Contribution to journal › Article › peer-review

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
Pages (from-to)	2427-2433
Number of pages	7
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	20
Publication status	Published - 21 Oct 1996

Keywords

METALLOSUPRAMOLECULAR CHEMISTRY
MOLECULES

Cite this

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title = "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.",

keywords = "METALLOSUPRAMOLECULAR CHEMISTRY, MOLECULES",

author = "M Mascal and Wood, {I G} and Begley, {M J} and Batsanov, {A S} and T Walsgrove and Slawin, {A M Z} and Williams, {D J} and Drake, {A F} and G Siligardi",

year = "1996",

month = oct,

day = "21",

language = "English",

pages = "2427--2433",

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

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T1 - Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles

AU - Mascal, M

AU - Wood, I G

AU - Begley, M J

AU - Batsanov, A S

AU - Walsgrove, T

AU - Slawin, A M Z

AU - Williams, D J

AU - Drake, A F

AU - Siligardi, G

PY - 1996/10/21

Y1 - 1996/10/21

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.

KW - METALLOSUPRAMOLECULAR CHEMISTRY

KW - MOLECULES

M3 - Article

SN - 0300-922X

SP - 2427

EP - 2433

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 20

ER -

Indole-fused tetraazacyclooctadecanes: Double-helical macrocycles

Abstract

Keywords

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