Helenanolide-type sesquiterpene lactones--III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules.

@article{Schmidt1997HelenanolidetypeSL,
  title={Helenanolide-type sesquiterpene lactones--III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules.},
  author={Thomas J{\"u}rgen Schmidt},
  journal={Bioorganic & medicinal chemistry},
  year={1997},
  volume={5 4},
  pages={
          645-53
        }
}
The reactivity of the two potential Michael addition sites of the helenanolide-type sesquiterpene lactone helenalin towards the physiological thiols glutathione (GSH) and cysteine (cys) in aqueous solution was investigated by 1H NMR spectroscopic experiments. In the presence of one molar equivalent of GSH, the reaction was shown to occur with high regio- and stereoselectivity at the beta-position of C-2 in the cyclopentenone ring. Addition to the exocyclic methylene group at the lactone ring… CONTINUE READING
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