14034-70-9

Upstream product

• 25100-13-4 dicyclohexylammonium sulphate 
• 59-56-3 β-D-glucose 1-phosphate 
• 108-91-8 cyclohexylamine 
• 59-56-3 mannose-1-phosphate 
• 530-26-7 D-Mannose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 90357-98-5 dibenzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate 
• 58526-05-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate 
• 4768-77-8 exo-3,4,6-tri-O-acetyl-1,2-O-(tert-butyl orthoacetyl)-α-D-glucopyranose 

Downstream Products

• 138385-94-1 α-D-mannopyranosyl 2,4-dinitrophenyl phosphate 
• 991-43-5 guanosine 5'-diphospho-D-mannose 

Relevant academic research and scientific papers

Facile enzymatic synthesis of sugar 1-phosphates as substrates for phosphorylases using anomeric kinases

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.

The cofactor Mg2+ - A key switch for effective continuous enzymatic production of GDP-mannose using recombinant GDP-mannose pyrophosphorylase

The aim of the presented work is the chemoenzymatic synthesis of GDP- mannose (GDP-Man). Mannose-1-phosphate (Man-1-P) is synthesised by a very convenient chemical method and is activated with GTP and recombinant GDP- mannose pyrophosphorylase (GDP-Man PP) to give GDP-Man. The productivity of the process is improved using reaction engineering techniques. Detailed kinetic studies, modelling of the reaction and simulations of different reaction systems revealed that besides a strong product inhibition the cofactor Mg2+ is a key switch for effective enzymatic synthesis. Using a two-stage cascade of enzyme membrane reactors, GDP-Man could be produced continuously with a space-time yield of 28 gL-1 d-1 and an enzyme consumption of 0.9 Ug-1, which means a six-fold improvement related to batch synthesis.

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

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.