Stability of Cyclic Imine Toxins: Interconversion of Pinnatoxin Amino Ketone and Pinnatoxin A in Aqueous Media

作者：Jackson Jeffrey J; Stivala Craig E; Iorga Bogdan I; Molgo Jordi; Zakarian Armen^*

来源：Journal of Organic Chemistry, 2012, 77(22): 10435-10440.

DOI：10.1021/jo301632d

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 pinnatozins 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.

• 出版日期2012-11-16