Synthesis of Sugars by Aldolase-Catalyzed Condensation Reactions

Article abstract of DOI:10.1021/jo00167a012

Dihydroxyacetone phosphate was prepared in 200-mmol scale from dihydroxyacetone by two procedures: reaction with phosphorus oxytrichloride and glycerol kinase catalyzed phosphorylation using ATP with in situ regeneration of ATP by phosphoenolpyruvate or acetyl phosphate.Dihydroxyacetone phosphate was converted to fructose 6-phosphate in 80percent yield by exposure to a mixture of co-immobilized triosephosphate isomerase and aldolase followed by acid hydrolysis of the condensation product fructose 1,6-bisphosphate.Fructose 6-phosphate was subsequently converted by chemical and enzymatic schemes into fructose, glucose 6-phosphate, and glucose.Practical procedures are described for the preparation of D- and L-glyceraldehyde 3-phosphate and for several hexoses labeled with 13C in the C-2 and C-2,5 positions.