Regio- and stereospecific syntheses and nitric oxide donor properties of (E)-9- and (E)-10-nitrooctadec-9-enoic acids.
[reaction: see text] Nitrated fatty acids act as endogenous peroxisome proliferator-activated receptor gamma (PPARgamma) ligands and nitric oxide (NO) donors. We describe the first specific preparation of the two regioisomers of nitrooleic acid, (E)-9-nitrooctadec-9-enoic acid (1) and (E)-10-nitrooctadec-9-enoic acid (2), from cis-cyclooctene and monomethyl azelate, respectively. These syntheses rely upon a Henry condensation between a nine-carbon nitro component and a nine-carbon aldehyde. Preliminary chemiluminescence NO detection studies reveal the ability of these nitrated fatty acids to release NO.
Gorczynski
Michael J
MJ
Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.
Huang
Jinming
J
King
S Bruce
SB
D049449:Luminescence; D015394:Molecular Structure; D009569:Nitric Oxide / Q000737:chemistry / Q000378:metabolism; D020030:Nitric Oxide Donors / Q000138:chemical synthesis* / Q000737:chemistry*; D009829:Oleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D020030:Nitric Oxide Donors; D009829:Oleic Acids; D009569:Nitric Oxide