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Revision of the Unstable Picrotoxinin Hydrolysis Product
Author(s) -
Tong Guanghu,
Shenvi Ryan A.
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202107785
Subject(s) - hydrolysis , chemistry , metabolite , degradation (telecommunications) , mistake , analogy , product (mathematics) , stereochemistry , organic chemistry , biochemistry , computer science , philosophy , telecommunications , linguistics , geometry , mathematics , political science , law
The plant metabolite picrotoxinin (PXN) is a widely used tool in neuroscience for the identification of GABAergic signaling. Its hydrolysis in weakly alkaline media has been observed for over a century and the structure of the unstable hydrolysis intermediate was assigned by analogy to the degradation product picrotoxic acid. Here we show this assignment to be in error and we revise the structure of the hydrolysis product by spectroscopic characterization in situ. Counterintuitively, hydrolysis occurs at a lactone that remains closed in the major isolable degradation product, which accounts for the longstanding mistake in the literature.