14034-70-9Relevant articles and documents
Facile enzymatic synthesis of sugar 1-phosphates as substrates for phosphorylases using anomeric kinases
Liu, Yuan,Nishimoto, Mamoru,Kitaoka, Motomitsu
, p. 1 - 4 (2015/02/19)
Three sugar 1-phosphates that are donor substrates for phosphorylases were produced at the gram scale from phosphoenolpyruvic acid and the corresponding sugars by the combined action of pyruvate kinase and the corresponding anomeric kinases in good yields. These sugar 1-phosphates were purified through two electrodialysis steps. α-d-Galactose 1-phosphate was finally isolated as crystals of dipotassium salts. α-d-Mannose 1-phosphate and 2-acetamido-2-deoxy-α-d-glucose 1-phosphate were isolated as crystals of bis(cyclohexylammonium) salts.
SYNTHESIS OF GLYCOSYL PHOSPHATES FROM SUGAR ORTHO ESTERS: FORMATION OF BIS(2,3,4,6-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL) PHOSPHATE, AND THE EFFECT OF SOLVENTS ON THE SYNTHESIS OF β-D-GLUCOPYRANOSYL PHOSPHATE
Salam, Mohammed A.,Behrman, Edward J.
, p. 83 - 90 (2007/10/02)
Reaction of exo-3,4,6-tri-O-acetyl-1,2-O-(tert-butyl orthoacetyl)-α-D-glucopyranose with phosphoric acid and phosphorus pentaoxide in oxolane gave 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate.Treatment of the reaction mixture with aqueous lithium hydroxide gave the expected β-D-glucopyranosyl phosphate.However, neutralization with ammonium hydroxide gave exclusively the phosphoric diester, namely, bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate.Formation of the diester was traced to the phosphorus pentaoxide in the initial reaction-mixture.A study of solvents showed that phosphorylation of the ortho ester proceeds rapidly in a variety of ethers and N,N-dimethylamides.
