Conformational analysis of the ergot alkaloids ergotamine and ergotaminine

Conformational analyses by 1H 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 CDCl3. two strong intramolecular hydrogen bonds fix the molecules in folded conformations, b...

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Published inJournal of medicinal chemistry Vol. 25; no. 8; pp. 937 - 942
Main Authors Pierri, L, Pitman, I. H, Rae, I. D, Winkler, D. A, Andrews, P. R
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.08.1982
Subjects
Chemical Phenomena
Chemistry
Ergotamine
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Stereoisomerism
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Summary:Conformational analyses by 1H 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 CDCl3. 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 CDCl3 solution.
Bibliography:ark:/67375/TPS-TGS0FD0Q-Z
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00350a010