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Stereospecific synthesis of (6R)- and (6S)-[6-2H1]-D-glucoses

✍ Scribed by Katsumi Kakinuma

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
233 KB
Volume
18
Category
Article
ISSN
0040-4039

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✦ Synopsis

Although carbohydrate metabolisms have been well studied and importance of carbohydrates as precursors of various natural products is widely understood, little attention has been paid from the stereochemical viewpoints for the fates of a prochiral hydroxymethyl group of &glucose or other carbohydrates in biological systems. To facilitate the stereochemical studies on the enzyme reactions, it is desirable to use stereospecifically labeled carbohydrates with hydrogen isotopes (*H and/or 3H) on the hydroxymethyl group. 1) So far, carbohydrates containing a chiral hydroxymethyl group have been prepared only by enzymic procedures, e.g. Q-glucose with a hydrogen isotope on C-l can be converted by phosphoglucose isomerase to &-fructose labeled in a stereospecifit manner at the C-l hydroxymethyl group, 2) which is further manipulated to various compounds such as phosphoenolpyruvate, dihydroxyacetone phosphate, etc., by glycolytic enzymes. 3) This communication describes, to the best of author's knowledge, the first chemical synthesis of g-glucose having the stereospecifically labeled chiral hydroxymethyl group, which posseses high usefulness and generality for preparation of quantities of such carbohydrate derivatives to provide a new tool for studies of the stereochemistry of carbohydrate metabolisms.

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