期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 52, 页码 16836-16843出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201357
关键词
natural products; NMR spectroscopy; ovatoxin-a; stereochemistry; structure elucidation
资金
- PRIN (Ministero dell'Istruzione, dell'Universita e della Ricerca, Rome, Italy) [2009JS5YX9_004]
- Regione Campania, Italy (Piano di monitoraggio annuale per il contenimento del rischio conseguente alla fioritura di Ostreopsis ovata nelle acque costiere della Campania-Attivita)
Ovatoxin-a is the main toxin produced by Ostreopsis ovata, a benthic dinoflagellate that has bloomed massively across the Mediterranean basin over the past years, inflicting both human and environmental suffering. Ovatoxin-a has recently been isolated from cultures of O. ovata and structurally identified as an analogue of palytoxin: in comparison with palytoxin, ovatoxin-a lacks three hydroxy groups at the 17-, 44- and 64-positions, but features an extra hydroxy functionality at the 42-position. Herein we report on the NMR-based elucidation of the stereochemistry of ovatoxin-a, which includes 7 stereogenic double bonds and 62 asymmetric carbon atoms. Understanding the full stereochemistry of ovatoxin-a is a step towards the elucidation of its mechanism of action on a molecular level.
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