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

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• 作者：Jeffrey J. Jackson ; Craig E. Stivala ; Bogdan I. Iorga ; Jordi Molg贸 ; Armen Zakarian
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：November 16, 2012
• 年：2012
• 卷：77
• 期：22
• 页码：10435-10440
• 全文大小：401K
• 年卷期：v.77,no.22(November 16, 2012)
• ISSN：1520-6904

文摘

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.