Abstract
Alkyne-modified phospholipids can be unambiguously identified and differentiated from native species in complex mixtures by formation of dicobalthexacarbonyl complexes. This reaction is specific for alkynes and is unaffected by other glycerophospholipid-related moieties. Enrichment of cells with alkyne-derivatized fatty acids or glycerophospholipids followed by solid-phase sequestration and release is a promising new method for unequivocally monitoring individual glycerophospholipids following incorporation into cells. This technique also facilitates lipidomic analysis of substrates and products.
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Acknowledgements
The authors thank P. Ivanova and D. Myers for technical assistance and many helpful conversations. This work was partially supported by the US National Institutes of Health (P01-ES013125 to H.A.B., L.J.M. and N.A.P.), a Vanderbilt Institute of Chemical Biology Pilot Program grant (H.A.B. and N.A.P.) and National Institutes of Health Grant Lipid Maps U54 GM69338 (H.A.B.).
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S.B.M. analyzed cell extract samples by mass spectrometry. K.A.T. and R.S. performed chemical synthesis, purification and analysis. S.B.M. and C.M.L. developed the alkyne lipid cobalt derivatization protocol. K.A.T. and S.B.M. developed the capture and release methodology. M.D.A. and C.A.R. contributed to the lipid enrichment procedures. L.J.M., N.A.P. and H.A.B. were responsible for overall project direction and experimental design. All authors discussed the results and modified the manuscript.
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Milne, S., Tallman, K., Serwa, R. et al. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat Chem Biol 6, 205–207 (2010). https://doi.org/10.1038/nchembio.311
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DOI: https://doi.org/10.1038/nchembio.311
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