The alkynylpyrrolidine 4 was made via a dearomatising cyclisation of an aromatic amide, and was elaborated by stannylcupration and palladium-catalysed coupling to achieve the first total synthesis of three members of the isodomoic acid family; the same alkyne can be envisaged as a precursor to several more of this class of amnesic shellfish toxins.
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http://dx.doi.org/10.1039/c1cc00048a | DOI Listing |
Harmful Algae
November 2024
The Arctic University Museum of Norway, UiT - the Arctic University of Norway, Lars Thørings veg 10, 9006 Tromsø, Norway. Electronic address:
Toxicon
September 2022
Fukushima College, 1-1 Chigoike Miyashiro, Fukushima, 960-0181, Japan. Electronic address:
To determine the species distribution of an amnesic shellfish poisoning (ASP) toxins-producing diatom Nitzschia navis-varingica outside its current restricted geographical distribution range in Asian coastal waters, samples were collected from two sites of Bootless Bay, located on southwest coast of Papua New Guinea near Port Moresby. A total of twenty-one strains of N. navis-varingica were isolated and the clonal cultures established.
View Article and Find Full Text PDFProc Natl Acad Sci U S A
February 2022
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California San Diego, La Jolla, CA 92093;
Domoic acid (DA), the causative agent of amnesic shellfish poisoning, is produced by select organisms within two distantly related algal clades: planktonic diatoms and red macroalgae. The biosynthetic pathway to isodomoic acid A was recently solved in the harmful algal bloom-forming diatom , establishing the genetic basis for the global production of this potent neurotoxin. Herein, we sequenced the 507-Mb genome of , the red macroalgal seaweed from which DA was first isolated in the 1950s, identifying several copies of the red algal DA () biosynthetic gene cluster.
View Article and Find Full Text PDFOrg Biomol Chem
September 2021
Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki-Aza-Aoba, Aoba-ku, Sendai 980-8572, Japan.
Domoic acid (1, DA), a member of the natural kainoid family, is a potent agonist of ionotropic glutamate receptors in the central nervous system. The chemical synthesis of DA and its derivatives requires considerable effort to establish a pyrrolidine ring containing three contiguous stereocenters. Recently, a biosynthetic cyclase for DA, DabC, was identified.
View Article and Find Full Text PDFToxins (Basel)
January 2021
Natural History Museum of Denmark, University of Copenhagen, Øster Farimagsgade 5, 1353 Copenhagen K, Denmark.
The Southern Ocean is one of the most productive ecosystems in the world. It is an area heavily dependent on marine primary production and serving as a feeding ground for numerous seabirds and marine mammals. Therefore, the phytoplankton composition and presence of toxic species are of crucial importance.
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