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Stability of cyclic imine toxins: interconversion of pinnatoxin amino ketone and pinnatoxin A in aqueous media.

Authors :
Jackson JJ
Stivala CE
Iorga BI
Molgó J
Zakarian A
Source :
The Journal of organic chemistry [J Org Chem] 2012 Nov 16; Vol. 77 (22), pp. 10435-40. Date of Electronic Publication: 2012 Nov 06.
Publication Year :
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.

Details

Language :
English
ISSN :
1520-6904
Volume :
77
Issue :
22
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
23116445
Full Text :
https://doi.org/10.1021/jo301632d