The synthesis of sucrose 6′-phosphate

Add time:08/15/2019    Source:sciencedirect.com

Sucrose 6′-phosphate, the monophosphate of sucrose which is an intermediate in the biosynthesis of sucrose, has been synthesised by an unambiguous route. The known sucrose 2,3,6,3′,4′-penta-acetate (3) was converted into 6′-O-tritylsucrose (5) which, on per-O-acetylation and detritylation, afforded crystalline sucrose 2,3,4,6,1′,3′,4′-hepta-acetate (8). Phosphorylation of 8 by means of cyanoethyl phosphate and dicyclohexylcarbodiimide, followed by removal of protecting groups, yielded sucrose 6′-phosphate (1), isolated as the barium and potassium salts. The synthetic compound was enzymically active towards wheat-germ UDP-D-glucose:D-fructose 6-phosphate 2-D-glucosyltransferase (sucrose 6′-phosphate synthetase).

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