About the project
Another twist in marine toxin’s structural saga. Researchers synthesize azaspiracid and uncover structural misassignment
https://cen.acs.org/articles/95/web/2017/12/Another-twist-marine-toxins-structural.html “This is an admirable chemical detective story and Craig Forsyth and his team deserve our congratulations for their meticulous work leading to the final structural revision of the azaspiracid structures,” Nicolaou says. “That they were able to decipher the last detail for the correct structure as they did, is a testament not only to their brilliant and scholarly work, but also to the current powerful state of the art of total synthesis and the modern high resolution analytical techniques that support it.” (Angew. Chem. Int. Ed.2017, DOI: 10.1002/anie.201711006; Angew. Chem. Int. Ed. 2017, DOI: 10.1002/anie.201711008).
Isolation, structure elucidation, relative LC-MS response, and in vitro toxicity of azaspiracids from the dinoflagellate Azadinium spinosum Kilcoyne, Jane; Nulty, Ciara; Jauffrais, Thierry; McCarron, Pearse; Herve, Fabienne; Foley, Barry; Rise, Frode; Crain, Sheila; Wilkins, Alistair L.; Twiner, Michael J.; et al. Journal of Natural Products (2014), 77(11), 2465-2474.
Epimers of Azaspiracids: Isolation, Structural Elucidation, Relative LC-MS Response, and in Vitro Toxicity of 37-epi-Azaspiracid-1 Kilcoyne, Jane; McCarron, Pearse; Twiner, Michael J.; Nulty, Ciara; Crain, Sheila; Quilliam, Michael A.; Rise, Frode; Wilkins, Alistair L.; Miles, Christopher O. Chemical Research in Toxicology (2014), 27(4), 587-600.
Conjugation of Microcystins with Thiols Is Reversible: Base-Catalyzed Deconjugation for Chemical Analysis Miles, Christopher O.; Sandvik, Morten; Nonga, Hezron E.; Ballot, Andreas; Wilkins, Alistair L.; Rise, Frode; Jaabaek, J. Atle H.; Loader, Jared I. Chemical Research in Toxicology (2016), 29(5), 860-870.
Preparation and Characterization of Cysteine Adducts of Deoxynivalenol. Ana Stanic, Silvio Uhlig, Anita Solhaug, Frode Rise, Alistair L. Wilkins, and Christopher O. Miles. J. Agric. Food Chem., 2016, 64 (23), 4777–4785.
Nucleophilic Addition of Thiols to Deoxynivalenol Stanic, Ana; Uhlig, Silvio; Solhaug, Anita; Rise, Frode; Wilkins, Alistair L.; Miles, Christopher O. Journal of Agricultural and Food Chemistry (2015), 63(34), 7556-7566.
Characterization of Deoxynivalenol-Gluthatione Conjugates Using Nuclear Magnetic Resonance Spectroscopy and Liquid Chromatography-High-Resolution Mass Spectrometry. Stanic, Ana; Uhlig, Silvio; Sandvik, Morten; Rise, Frode; Wilkins, Alistair L.; Miles, Christopher O. Journal of Agricultural and Food Chemistry (2016), 64(36), 6903-6910.
Tools
The AVI600, AVII600 and AVIIIHD800 nmr instruments at the University of Oslo NMR Center are used in these studies.