Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5225693 | Tetrahedron | 2009 | 11 Pages |
Abstract
Syntheses of fluorinated mucin core 6 disaccharides and core 2 trisaccharides modified at the C-3 or C-4 position of the pertinent glucosamine residue required for mechanistic study of glycosyltransferases and sulfotransferases involved in the biosynthesis of O-glycans are reported. Novel fluorinated glucosaminyl donors were synthesized from 2-naphthylmethyl β-d-N-acetylglucosamine (β-O-NAP-GlcNAc) via double inversion of the C-3 or C-4 configuration. A one-step β-alkylation of GlcNAc was reported for the first time to afford β-O-NAP-GlcNAc in high yield, which constitutes the cornerstone of the synthetic strategy based on NAP-glycosides in oligosaccharides synthesis.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jun Xue, Vipin Kumar, Sirajud D. Khaja, E.V. Chandrasekaran, Robert D. Locke, Khushi L. Matta,