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.
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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 J. Am. Chem. Soc. 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).
