Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl Phosphate

Authors: Miyazaki, Tatsuo; Hiyoshi, Daisuke; Izumi, Masayuki; Hashimoto, Hironobu; Yuasa, Hideya

Source: Letters in Organic Chemistry, Volume 5, Number 7, October 2008 , pp. 576-578(3)

Publisher: Bentham Science Publishers

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Abstract:

The fucosyltransferase-catalyzed 5-thiofucosylation reaction suffered from limitations in the β-selective synthesis of GDP-5-thiofucose, a donor substrate. We found that the use of electronegatively-substituted benzoate groups for 5-thiofucose protection improved the β-selectivity in the phosphorylation step. We thus achieved the synthesis of 5-thio-β- L-fucosyl phosphate in 50% yield from 5-thiofucose, using the 3,5-dinitrobenzoyl group.

Keywords: 5-thiofucose; phosphorylation; glycosyl phosphate; stereoselectivity

Document Type: Research article

DOI: 10.2174/157017808785982130