Synthesis of Novel, Fluorescently Tagged Analogs of Glycosylphosphatidylinositol (GPI) Anchors

Abstract

Glycosylphosphatidylinositol (GPI) anchors are a group of complex glycolipids that attach extracellular proteins and glycoproteins to the eukaryotic cell outer membrane. To better understand GPI anchorage, it is necessary to have access to homogeneous, structurally defined, and functionalized GPIs and GPI analogs. In this regard, chemical synthesis is necessary, as GPI anchors are rather scarce and heterogeneous in natural sources. Three GPI analogs with phosphoglycerolipids linked to the pseudodisaccharide core and their fluorescein conjugates were prepared in this work as a small tool set useful for probing how the lipid composition and carbohydrate anomeric configuration may affect the properties of GPI anchors.

Keywords:

• Glycosylphosphatidylinositol
• GPI anchor
• Phospholipid
• Glycolipid
• Fluorescein
• Fluorescent tag

ACKNOWLEDGMENT

The authors thank the National Science Foundation (NSF CHE-1053848) for financial support.