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Synthesis and Characterization of the Enantiomerically Pure cis ‐ and trans ‐2,4‐Dioxa‐3‐fluoro‐3‐phosphadecalins as Inhibitors of Acetylcholinesterase
Author(s) -
Wächter Michael,
Rüedi Peter
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800335
Subject(s) - decane , diisopropyl fluorophosphate , chemistry , acetylcholinesterase , stereoselectivity , enzyme , stereochemistry , organic chemistry , catalysis
The title compounds, the P(3) ‐axially‐ and P(3)‐ equatorially‐substituted cis ‐ and trans ‐configured 3‐fluoro‐2,4‐dioxa‐3‐phosphadecalin 3‐oxides (=3‐fluoro‐2,4‐dioxa‐3‐phosphabicyclo[4.4.0]decane 3‐oxides) have been prepared (ee>99%) and fully characterized. The compounds are irreversible inhibitors of acetylcholinesterase, and both the kinetic data and the mechanisms of the inhibition are determined by a novel enzyme‐kinetic approach that is described in the preceding report. The inhibitors display pronounced stereoselectivity, and several of them are significantly stronger than diisopropyl fluorophosphate that is generally used as a potent standard.