Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage.

ABSTRACT: To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.

SUBMITTER: Lankalapalli RS 

PROVIDER: S-EPMC2741175 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature