Synthesis and characterization of a highly fluorescent peptidyl-phosphatidylethanolamine.
The synthesis of a fluorescent lipid for use in studies of immune recognition of model membranes is described. The molecule has the basic structure HAPTEN-SPACER-LIPID, where fluorescein is the hapten, an oligopeptide (triglycine) is the spacer, and dipalmitoylphosphatidylethanolamine (DPPE) is the lipid. The spacer, which is necessary for immunological reactivity, is first linked via a peptide bond to DPPE. The free N-terminus of the peptidyl-DPPE is then reacted with 5-dichlorotriazinylaminofluorescein (DCTAF) to yield fluoresceinchlorotriazinyltriglycyl-DPPE (FG3P). The structure is confirmed by mass spectrometry and Fourier transform NMR. When FG3P is incorporated into phospholipid vesicles it retains the brilliant fluorescence and high-affinity immunological reactivity of fluorescein. The general synthesis scheme may prove useful in other membrane and lipoprotein applications.
D019793:Fluorescein; D005452:Fluoresceins; D005456:Fluorescent Dyes; D005998:Glycine; D013058:Mass Spectrometry; D009842:Oligopeptides; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis*
D005452:Fluoresceins; D005456:Fluorescent Dyes; D009842:Oligopeptides; D010714:Phosphatidylethanolamines; C007510:1,2-dipalmitoyl-3-phosphatidylethanolamine; D005998:Glycine; D019793:Fluorescein