Reprint of: “Synthetic lipids and their role in defining macromolecular assemblies”

• BODIPY-cholesterol serves as a fluorescent probe of cholesterol localization.
• Ceramide analogs illustrate ceramide channel structure activity relationships.
• Alkyl glycerol phosphate stereoisomers probe receptor stereospecificity.

Lipids have a variety of physiological roles, ranging from structural and biophysical contributions to membrane functions to signaling contributions in normal and abnormal physiology. This review highlights some of the contributions made by Robert Bittman to our understanding of lipid assemblies through the production of synthetic lipid analogs in the sterol, sphingolipid, and glycolipid classes. His contributions have included the development of a fluorescent cholesterol analog that shows strong functional analogies to cholesterol that has allowed live imaging of cholesterol distribution in living systems, to stereospecific synthetic approaches to both sphingolipid and glycolipid analogs crucial in defining the structure–activity relationships of lipid biological targets.

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