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 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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
}
TY - JOUR
T1 - Indole-fused tetraazacyclooctadecanes
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.
UR - http://www.scopus.com/inward/record.url?scp=33748956505&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33748956505&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:33748956505
SP - 2427
EP - 2433
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1470-4358
IS - 20
ER -