Jackson_2012_J.Org.Chem_77_10435

Reference

Title : Stability of cyclic imine toxins: interconversion of pinnatoxin amino ketone and pinnatoxin A in aqueous media - Jackson_2012_J.Org.Chem_77_10435
Author(s) : Jackson JJ , Stivala CE , Iorga BI , Molgo J , Zakarian A
Ref : J Org Chem , 77 :10435 , 2012
Abstract :

Pinnatoxins belong to the cyclic imine (CI) group of marine toxins with a unique toxicological profile. The need for structural integrity of the aliphatic 7-membered cyclic imine for the potent bioactivity of pinnatoxins has been experimentally demonstrated. In this study, we probe interconversion of the natural cyclic imine and its open form, pinnatoxin A amino ketone (PnTX AK), under physiologically relevant aqueous conditions. Our studies demonstrate the high stability of PnTX A. The unusual stability of the imine ring in PnTX A has implications for its oral toxicity and detoxification. These studies, as well the access to PnTX amino ketone, were enabled by the total synthesis of (+)-pinnatoxin A completed previously in our laboratory.

PubMedSearch : Jackson_2012_J.Org.Chem_77_10435
PubMedID: 23116445

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Citations formats

Jackson JJ, Stivala CE, Iorga BI, Molgo J, Zakarian A (2012)
Stability of cyclic imine toxins: interconversion of pinnatoxin amino ketone and pinnatoxin A in aqueous media
J Org Chem 77 :10435

Jackson JJ, Stivala CE, Iorga BI, Molgo J, Zakarian A (2012)
J Org Chem 77 :10435