Enzymatic synthesis of stable, odorless, and powdered furanone glucosides by sucrose phosphorylase.
Sucrose phosphorylase from Leuconostoc mesenteroides catalyzed transglucosylation 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)-furanone or 5-ethyl-4-hydroxy-2-methyl-3(2H)-furanone (EHMF) were used as acceptors, their transfer ratios were more than 45%. In the case of glucosylation of HDMF, the major transfer product was identified as 2,5-dimethyl-3(2H)-furanone 4-O-alpha-D-glucopyranoside (DMF-G). In the case of glucosylation 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-glucopyranoside (2E5MF-G) and 5-ethyl-2-methyl-3(2H)-furanone 4-O-alpha-D-glucopyranoside (5E2MF-G) on the bases of spectrometric investigations. These glucosides 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 glucosylated EHMF (EMF-G) were white odorless powders, though aglycone EHMF was a pale yellow syrup like a caramel with an intense sweet odor. Although DMF-G and EMF-G showed little radical-scavenging activity, hydrolyzates of these glucosides by an intestinal acetone powder from pigs had antioxidative activity as well as their aglycones. It was suggested that these glucosides improved some physical properties and may become prodrugs by glucosylation.
Kitao
S
S
Research and Development Division, Kikkoman Corporation, Chiba, Japan. s-kitao@zb3.so-net.ne.jp
Matsudo
T
T
Sasaki
T
T
Koga
T
T
Kawamura
M
M
D000975:Antioxidants / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000737:chemistry* / Q000378:metabolism; D005964:Glucosyltransferases / Q000378:metabolism*; D006868:Hydrolysis; D007934:Leuconostoc / Q000201:enzymology; D009812:Odorants; D011355:Prodrugs / Q000737:chemistry / Q000378:metabolism; D012440:Saccharomyces / Q000201:enzymology; D013379:Substrate Specificity
D000975:Antioxidants; D005663:Furans; D011355:Prodrugs; C058427:furaneol; D005964:Glucosyltransferases; C025901:sucrose phosphorylase; C112945:4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone