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Bildung von Enolether‐Epoxiden durch Einwirkung von (9 S ,10 E ,12 Z )‐Hydroperoxyoctadecadiensäure auf Plasmalogene
Author(s) -
Scheick Cordula,
Spiteller Gerhard
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301202
Subject(s) - chemistry , enol , epoxide , enol ether , methanol , aldehyde , medicinal chemistry , ether , stereochemistry , organic chemistry , catalysis
Formation of Enol Ether Epoxides by Reaction of (9 S ,10 E ,12 Z )‐Hydroperoxyoctadecadienoic Acid with Plasmalogens (9 S ,10 E ,12 Z )‐Hydroperoxyoctadecadienoic acid ( 8a ) oxidizes enol ethers (e.g. 2 and neutral plasmalogens 3 ) under physiological conditions (pH = 6.6, room temperature). The reaction products, unstable enol ether epoxides 9a and 10a , react as recently demonstrated with methanol to α‐hydroxyaldehyde dialkyl acetals 11a or with 1,2‐ethanedithiol to 2‐(α‐hydroxyalkyl)dithiolans 13a which can be detected by GC/MS after trimethylsilylation. If [ 18 O 2 ]‐(9 S ,10 E ,12 Z )‐hydroperoxy‐octadecadienoic acid ( 8b ) is used instead of 8a one atom of 18 O is incorporated into the enol ether epoxide and found in the α‐hydroxy group of the aldehyde derivatives 11 and 13 .