Ex Uno Plura: Differential Labeling of Phospholipid Biosynthetic Pathways with a Single Bioorthogonal Alcohol

Biochemistry
Timothy W BumpusJeremy M Baskin

Abstract

Imaging approaches that track biological molecules within cells are essential tools in modern biochemistry. Lipids are particularly challenging to visualize, as they are not directly genetically encoded. Phospholipids, the most abundant subgroup of lipids, are structurally diverse and accomplish many cellular functions, acting as major structural components of membranes and as signaling molecules that regulate cell growth, division, apoptosis, cytoskeletal dynamics, and numerous other physiological processes. Cells regulate the abundance, and therefore bioactivity, of phospholipids by modulating the activities of their biosynthetic enzymes. Thus, techniques that enable monitoring of flux through individual lipid biosynthetic pathways can provide key functional information. For example, the choline analogue propargylcholine (ProCho) can report on de novo biosynthesis of phosphatidylcholine by conversion to an alkynyl lipid that can be imaged following click chemistry tagging with an azido fluorophore. We report that ProCho is also a substrate of phospholipase D enzymes-which normally hydrolyze phosphatidylcholine to generate the lipid second messenger phosphatidic acid-in a transphosphatidylation reaction, generating the identic...Continue Reading

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Citations

Jul 18, 2019·Proceedings of the National Academy of Sciences of the United States of America·Dongjun LiangJeremy M Baskin
Jan 31, 2020·The Journal of Cell Biology·Reika Tei, Jeremy M Baskin
Jul 22, 2020·Chemical Society Reviews·Judith FloresNeal K Devaraj
Sep 9, 2020·Chemistry and Physics of Lipids·Christelle F AncajasMichael D Best
Mar 13, 2019·ACS Chemical Biology·Florian MayerthalerAlbert A Antolin

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