Linoleic Acid Alkyne

Linoleic acid alkyne is an ω-alkyne derivative of linoleic acid. The ω-alkyne moiety allows Cu(I)-catalyzed cycloaddition chemistry with other molecules containing an azide group.[1],[2] Linoleic acid alkyne has been used in experiments focusing on the biological roles of linoleic acid.[3],[4] Alternatively, this modified lipid can be used to synthesize other alkyne-containing products, such as glycerophospholipids, for click chemistry.[5]

Reference:
[1]. Gaebler, A., Penno, A., Kuerschner, L., et al. A highly sensitive protocol for microscopy of alkyne lipids and fluorescently tagged or immunostained proteins. J. Lipid. Res. 57(10), 1934-1947 (2016).
[2]. Grammel, M., and Hang, H.C. Chemical reporters for biological discovery. Nat. Chem. Biol. 9(8), 475-484 (2013).
[3]. Beavers, W.N., Serwa, R., Shimozu, Y., et al. ω-Alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations. Journal of the American Chemical Society 136(32), 11529-11539 (2014).
[4]. Windsor, K., Genaro-Mattos, T.C., Kim, H.-Y.H., et al. Probing lipid-protein adduction with alkynyl surrogates: application to Smith-Lemli-Opitz syndrome. J. Lipid. Res. 54(10), 2842-2850 (2013).
[5]. Milne, S.B., Tallman, K.A., Serwa, R., et al. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat. Chem. Biol. 6(3), 205-207 (2010).