Conformational analysis of the ergot alkaloids ergotamine and ergotaminine

L Pierri, I H Pitman, Ian Rae, David Winkler, Peter R Andrews

Research output: Contribution to journalArticleResearchpeer-review

48 Citations (Scopus)

Abstract

Conformational analyses by 'H NMR and potential-energy calculations are reported for the ergot alkaloids ergotamine and ergotaminine, both as free bases and as the protonated species. In the neutral forms in CDCl,, two strong intramolecular hydrogen bonds fix the molecules in folded conformations, but the protonated species adopt a more extended conformation, with a single intramolecular hydrogen bond. Of the 24 alternative conformations available to ergotamine, the most likely biologically active species in environments with low dielectric constants, e.g., the presumed ergotamine binding site, is the folded, hydrogen-bonded conformation observed for the neutral molecule in CDC13 solution.
Original languageEnglish
Pages (from-to)937-942
Number of pages6
JournalJournal of Medicinal Chemistry
Volume25
Issue number8
DOIs
Publication statusPublished - 1982

Cite this

Pierri, L., Pitman, I. H., Rae, I., Winkler, D., & Andrews, P. R. (1982). Conformational analysis of the ergot alkaloids ergotamine and ergotaminine. Journal of Medicinal Chemistry, 25(8), 937-942. https://doi.org/10.1021/jm00350a010
Pierri, L ; Pitman, I H ; Rae, Ian ; Winkler, David ; Andrews, Peter R. / Conformational analysis of the ergot alkaloids ergotamine and ergotaminine. In: Journal of Medicinal Chemistry. 1982 ; Vol. 25, No. 8. pp. 937-942.
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abstract = "Conformational analyses by 'H NMR and potential-energy calculations are reported for the ergot alkaloids ergotamine and ergotaminine, both as free bases and as the protonated species. In the neutral forms in CDCl,, two strong intramolecular hydrogen bonds fix the molecules in folded conformations, but the protonated species adopt a more extended conformation, with a single intramolecular hydrogen bond. Of the 24 alternative conformations available to ergotamine, the most likely biologically active species in environments with low dielectric constants, e.g., the presumed ergotamine binding site, is the folded, hydrogen-bonded conformation observed for the neutral molecule in CDC13 solution.",
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Pierri, L, Pitman, IH, Rae, I, Winkler, D & Andrews, PR 1982, 'Conformational analysis of the ergot alkaloids ergotamine and ergotaminine', Journal of Medicinal Chemistry, vol. 25, no. 8, pp. 937-942. https://doi.org/10.1021/jm00350a010

Conformational analysis of the ergot alkaloids ergotamine and ergotaminine. / Pierri, L; Pitman, I H; Rae, Ian; Winkler, David; Andrews, Peter R.

In: Journal of Medicinal Chemistry, Vol. 25, No. 8, 1982, p. 937-942.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - Conformational analysis of the ergot alkaloids ergotamine and ergotaminine

AU - Pierri, L

AU - Pitman, I H

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AU - Winkler, David

AU - Andrews, Peter R

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AB - Conformational analyses by 'H NMR and potential-energy calculations are reported for the ergot alkaloids ergotamine and ergotaminine, both as free bases and as the protonated species. In the neutral forms in CDCl,, two strong intramolecular hydrogen bonds fix the molecules in folded conformations, but the protonated species adopt a more extended conformation, with a single intramolecular hydrogen bond. Of the 24 alternative conformations available to ergotamine, the most likely biologically active species in environments with low dielectric constants, e.g., the presumed ergotamine binding site, is the folded, hydrogen-bonded conformation observed for the neutral molecule in CDC13 solution.

U2 - 10.1021/jm00350a010

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