Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage.
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.
Lankalapalli
Ravi S
RS
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Eckelkamp
Joseph T
JT
Sircar
Debajit
D
Ford
David A
DA
Subbaiah
Papasani V
PV
Bittman
Robert
R
D000475:Alkenes / Q000737:chemistry; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D005609:Free Radicals / Q000737:chemistry; D007495:Iridium / Q000737:chemistry; D015227:Lipid Peroxidation; D008958:Models, Molecular; D015394:Molecular Structure; D010955:Plasmalogens / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D000475:Alkenes; D000975:Antioxidants; D005609:Free Radicals; D010955:Plasmalogens; D014753:Vinyl Compounds; C100195:vinyl ether; D007495:Iridium