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Synthesis and characterization of a 13C-labeled α-mannosyl glycolipid analog from [13C]glucose

✍ Scribed by Brian J. Hare; Charles R. Sanders II; Stephen E. McIntyre; James H. Prestegard

Book ID
103042319
Publisher
Elsevier Science
Year
1993
Tongue
English
Weight
248 KB
Volume
66
Category
Article
ISSN
0009-3084

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✦ Synopsis

A method is described for the synthesis of a [13C]c~-mannosyl glycolipid analog from [13C]glucose. After acetylation and reduction of glucose (U-13C6, 30%) to tri-O-acetyl-D-glucal (U-13C6, 30%), addition of the nucleophile 2-[2-[2-[2-(tetradecyloxy)ethoxy]ethoxy]ethoxy]-ethanol (tetra-decyltetraglycol) yields the rearrangement product t~-tetradecyltetraglycol 2,3-dideoxy-4,6-di-O-acetyl-D-gluco-pyranoside (U)3C6, 30%). The rearrangement product is oxidized with osmium tetroxide to produce tetradecyltetraglycol c~-mannoside (U-~3C 6, 30%). The interaction of the glycolipid with the plant lectin concanavalin A is characterized by a vesicle agglutination assay.

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