Docosahexaenoic acid alkyne is an ω-alkyne derivative of docosahexaenoic acid . The ω-alkyne moiety allows Cu(I)-catalyzed cycloaddition chemistry with molecules containing an azide group. [1] [2] Alternatively, this modified lipid can be used to synthesize other alkyne-containing products, such as glycerophospholipids, for click chemistry. [3] ω-Alkyne lipid derivatives, such as docosahexaenoic acid alkyne, can also be used to track fatty acid metabolism in cells via click chemistry linkage to fluorophores.[4]
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]. 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).
[4]. Thiele, C., Papan, C., Hoelper, D., et al. Tracing fatty acid metabolism by click chemistry. ACS Chem Biol. 7(12), 2004-2011 (2012).