Design and Synthesis of a Doubly Functionalized Core Structure of a Glycosylphosphatidylinositol Anchor Containing Photoreactive and Clickable Functional Groups

J Org Chem. 2022 Jul 15;87(14):9419-9425. doi: 10.1021/acs.joc.2c00901. Epub 2022 Jun 29.

Abstract

A bifunctional derivative of the core structure of glycosylphosphatidylinositol (GPI) anchors having a clickable alkynyl group and a photoreactive diazirine group attached to the GPI glucosamine and lipid moieties, respectively, was synthesized from myo-inositol, d-glucosamine, and (R)-1,2-O-acetonized glycerol. The target molecule should be useful for the investigation of GPI-interacting components in the cell membrane that play a key role in the signal transduction and other biological functions of GPI-anchored proteins.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Glucosamine
  • Glycosylphosphatidylinositols* / chemistry
  • Glycosylphosphatidylinositols* / metabolism
  • Inositol / chemistry
  • Proteins* / chemistry

Substances

  • Glycosylphosphatidylinositols
  • Proteins
  • Inositol
  • Glucosamine