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

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-acetoni...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-07, Vol.87 (14), p.9419-9425
Main Authors: Mullapudi, Venkanna Babu, Craig, Kendall C., Guo, Zhongwu
Format: Article
Language:English
Subjects:
Glucosamine
Glycosylphosphatidylinositols - chemistry
Glycosylphosphatidylinositols - metabolism
Inositol - chemistry
Proteins - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00901