Transglucosylation with 6'-chloro-6'-deoxysucrose and immobilized isomaltulose-producing microorganisms using 2,2-dimethyl-1,3-dioxolane-4-methanol and its related compounds as acceptors. Steric and chemical requirement of the glucosyl acceptor.
Enantioselective and diastereoselective alpha-D-glucosylation of 2,3-O-isopropylidene-erythritol was observed in transglucosylation with a synthetic donor using three kinds of immobilized isomaltulose-producing microorganisms. Several related compounds, including an 2,3-O-isopropylidenated aldotetrose dimethyl dithioacetal and an aldotetronic acid ester were also glucosylated in moderate or good yield, depending on the microorganism utilized. Steric as well as functional group factors are discussed in relation to the substrate specificity of the glucosyl acceptor.
Kakinuma
H
H
Department of Life Science, Tokyo Institute of Technology, Yokohama, Japan.
Tsuchiya
Y
Y
Tanaka
M
M
Horito
S
S
Hashimoto
H
H
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004148:Dioxolanes; D004800:Enzymes, Immobilized; D004896:Erythritol / Q000031:analogs & derivatives*; D006031:Glycosylation; D007202:Indicators and Reagents; D007534:Isomaltose / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013237:Stereoisomerism; D013379:Substrate Specificity; D013395:Sucrose / Q000031:analogs & derivatives*; D000520:alpha-Glucosidases
C091286:2,3-O-isopropylideneerythritol; D004148:Dioxolanes; D004800:Enzymes, Immobilized; D007202:Indicators and Reagents; C024356:2,2-dimethyl-1,3-dioxolane-4-methanol; D013395:Sucrose; D007534:Isomaltose; D000520:alpha-Glucosidases; C015744:6-chloro-6-deoxysucrose; D004896:Erythritol; C008189:isomaltulose