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Synthesis Of Labeled Glycosyl Phosphatidyl Inositol (GPI) Anchors

✍ Scribed by Thomas G. Mayer; Ralf Weingart; Florian Münstermann; Toshinari Kawada; Teymuras Kurzchalia; Richard R. Schmidt


Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
449 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis


The exploration of the molecular and structural basis for the amino group of the glucosamine residue (2b-position) and a free amino group at the 6b-position. The 6b-amino group was sorting of GPI-anchored proteins is based on labeled partial structures of GPIЈs which can be incorporated into the GPI used for the ligation of the 3-(7-nitrobenzofurazan-4-yl)aminopropanoyl group as a fluorescent label, the 5-azido-2-anchor biosynthesis and cellular transport systems. To this end, from mannosyl donor 6 and the D-glucosaminyl-(1Ǟ6)-nitrobenzoyl and 4-azidophenylaminothiocarbonyl groups as photolabels, and the 4-azido-2-hydroxybenzoyl group as a D-myo-inositol derivative 7 as acceptor, the pseudotrisaccharide 8 was prepared. Compound 8 was transformed radiolabel after the introduction of radioactive iodine by an electrophilic aromatic substitution. Thus, after acid-catalyzed into the GPI partial structures 5a,b which contain the pseudotrisaccharide ligated to two different phosphatidyl removal of the protective groups, the unprotected target molecules 1-4 were obtained. residues. Compounds 5a,b have Boc protection at the 2-


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