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Research Article Open access CC BY 4.0

Mechanisms of the Aqueous Solvolysis of the Ring-opening of the Lactone Ring of Goniodomin A

B. Andes Hess Jr., Lidia Smentek

International Research Journal of Pure and Applied Chemistry · pp. 9–16 · Published 28 Nov 2022

10.9734/irjpac/2022/v23i6792

Abstract

The phycotoxin Goniodomin A is a Dinoflagellate of the Alexandrium genus and is a macrocyclic lactone. It is found widely in sea water and is known to open slowly the lactone in water. The cleavage of the lactone is sensitive to the pH of the water. As one changes the pH from ~6 to 8 its solvolytic rate dramatically increases. Treatment of kinetic data previously published indicates that there are two competing first-order reactions, an SN­1 and an intramolecular SN2, which is a pseudo first-order reaction.

Marine phytotoxin mechanism of lactone hydrolysis lactone epoxide carbocation nucleophilic reactions

References (7)

  1. 1 Goniodomin a, a novel polyether macrolide from the dinoflagellate goniodoma pseudogoniaulax [DOI]
  2. 2 Production of goniodomin A by the planktonic, chain-forming dinoflagellate Alexandrium monilatum (Howell) Balech isolated from the Gulf Coast of the United States [DOI]
  3. 3 Morphological and phylogenetic data do not support the split of Alexandrium into four genera [DOI]
  4. 4 A Screening Tool for the Direct Analysis of Marine and Freshwater Phycotoxins in Organic SPATT Extracts from the Chesapeake Bay [DOI]
  5. 5 Assignment of the Absolute Configuration of Goniodomin A by NMR Spectroscopy and Synthesis of Model Compounds [DOI]
  6. 6 First report of goniodomin A production by the dinoflagellate Alexandrium pseudogonyaulax developing in southern Mediterranean (Bizerte Lagoon, Tunisia) [DOI]
  7. 7 Algal Toxin Goniodomin A Binds Potassium Ion Selectively to Yield a Conformationally Altered Complex with Potential Biological Consequences [DOI]

Cited by 3

Goniodomic Acid, a Transient Oxirane Intermediate in the Conversion of the Macrolide Algal Toxin Goniodomin A to Seco Acids

Constance M. Harris, Bernd Krock, Thomas M. Harris · Chemical Research in Toxicology · 2024

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