Fluorocarbohydrates

Add time:07/22/2019    Source:sciencedirect.com

6-Deoxy-6-fluoro-α-d-galactose (1) was converted by conventional methods into crystalline 2,3,4-tri-O-acetyl-6-deoxy-6-fluoro-α-d-galactosyl bromide (2). Treatment of 2 with methanol-silver carbonate gave the methyl β-glycoside and reaction with silver diphenyl phosphate, followed by hydrogenolysis and deacetylation, gave 6-deoxy-6-fluoro-α-d-galactosyl dipotassium phosphate (6). A product chromatographically identical with 6 resulted when 1 was incubated with galactokinase and ATP at 37° and pH 6.8. Reduction of1 with sodium borohydride gave 1-deoxy-l-fluoro-l-galactitol (7) which was also formed, by the action of polyol dehydrogenase, when rabbit-lens capsules were incubated with 1. Biological reduction of 1 proceeds ≈3 times faster than that of d-galactose.

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