Chemistry of the shellfish toxin domoic acid: characterization of related compounds

Five new compounds related to the neurotoxin domoic acid have been characterized by spectroscopic methods. They include a diastereoisomer that occurs naturally with domoic acid in mussels and four hydrogenation products. The stereochemistry of the two epimeric tetrahydro derivatives could not be ass...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 72; no. 2; pp. 430 - 436
Main Authors Walter, John A, Falk, Michael, Wright, Jeffrey L.C
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.02.1994
National Research Council of Canada
Subjects
Analytical, structural and metabolic biochemistry
Aromatic and heterocyclic compounds
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Heterocyclic compounds, pigments
Other biological molecules
Five membered ring
Shellfish
Molecular structure
Nitrogen heterocycle
Neurotoxin
Isolation
NMR spectrum
Ethylenic compound
Pyrrolidine derivatives
Conformation
Tricarboxylic acid
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Summary:Five new compounds related to the neurotoxin domoic acid have been characterized by spectroscopic methods. They include a diastereoisomer that occurs naturally with domoic acid in mussels and four hydrogenation products. The stereochemistry of the two epimeric tetrahydro derivatives could not be assigned on the basis of the NMR data alone because of high conformational flexibility. However, a clear-cut assignment was possible by molecular modelling in combination with the NMR data.
ISSN:0008-4042
1480-3291
DOI:10.1139/v94-064