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Stereospecificity of linoleic acid hydroperoxide isomerase from corn germ
Author(s) -
Gardner H. W.
Publication year - 1979
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02533872
Subject(s) - chemistry , nucleophile , linoleic acid , stereospecificity , substrate (aquarium) , nucleophilic substitution , isomerase , stereochemistry , solvent , medicinal chemistry , organic chemistry , fatty acid , enzyme , catalysis , biology , ecology
Linoleic acid hydroperoxide isomerase from corn germ inverted the stereoconfiguration of its substrate. 9‐D(S)‐Hydroperoxy‐ trans ‐10, cis ‐12‐octadecadienoic acid was converted to 10‐oxo‐9‐L(R)‐hydroxy‐ cis ‐12‐octadecenoic acid. Presumably, the H 2 O solvent of OH − acted as a nucleophile. In the presence of another nucleophile, linoleate, the 9‐D(S)‐hydroperoxide was transformed into 9‐L(R)‐linoleoyloxy‐10‐oxo‐ cis ‐12‐octadecenoic acid. The substitution of nucleophiles from the incubation solution and the inversion of stereoconfiguration at carbon‐9 are consistent with a bimolecular nucleophilic substitution (S N 2) mechanism.