Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase

Sucrose phosphorylase from Leuconostoc mesenteroides catalyzed transglucosy lation from sucrose to 4-hydroxy-3(2H)-furanone derivatives, When 4-hydroxy -2,5-dimethyl-3(2H)-furanone (HDMF) and 2-ethyl-4-hydroxy-5-methyl-3(2H)-fu ranone or 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone (EHMF) were used as acc eptors, their transfer ratios were more than 45 %. In the case of glucosyla tion of HDMF, the major transfer product was identified as 2,5-dimethyl-3(2 H)-furanone 4-O-alpha-D-glucopyranoside (DMF-G). In the case of glucosylati on of EHMF, two major transfer products were obtained, and their structures were identified as 2-ethyl-5-methyl-3(2H)-furanone 4-O-alpha-D-glucopyrano side (2E5MF-G) and 5-ethyl-2-methyl-3(2H)-furanone 4-O-alpha-D-glucogyranos ide (5E2MF-G) on the bases of spectrometric investigations. These glucoside s were more stable than each aglycone. The glucosylated HDMF, DMF-G, was an odorless chemical, on the other hand, HDMF had a pineapple flavor. The glu cosylated EHMF (EMF-G) were white odorless powders, though aglycone EHMF wa s a pale yellow syrup like a caramel with an intense sweet odor. Although D MF-G and EMF-G showed little radical-scavenging activity, hydrolyzates of t hese glucosides by an intestinal acetone powder from pigs had antioxidative activity as well as their aglycones. It was suggested that these glucoside s improved some physical properties and may become prodrugs by glucosylatio n.