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
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).
