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- W2000599344 abstract "Pseudopterolide, a marine natural product processing a vinyl epoxide, has been shown to inhibit a variety of biological processes including cell division. We examined the ability of pseudopterolide to add to the sulfhydryl groups of a number of thiol-containing substances and found that it initially binds covalently to the sulfhydryl groups via an S N 2′ addition of sulfur to the α,β-unsaturated lactone with concomitant opening of the epoxide. Subsequent addition of the sulfhydryl group to the exocyclic enone results in the formation of a 1,2-adduct via an initial Michael addition reaction followed by an apparent intramolecular S N′ elimination. We suggest that the biological actions of pseudopterolide may be caused by the addition of this compound to the thiol groups of biologically active molecules. Reactions of sulfhydryl groups of a number of thiol-containing substances with pseudopterolide lead to a 1,4-,1,2- or a diadduct." @default.
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- W2000599344 date "1994-01-01" @default.
- W2000599344 modified "2023-09-26" @default.
- W2000599344 title "Thiophilic reactions of pseudopterolide: Potential implications for its biological activity" @default.
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- W2000599344 doi "https://doi.org/10.1016/s0040-4020(01)85501-0" @default.
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