Chemoenzymatic synthesis of n-hexyl and O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranosides.
Direct beta-glucosidation between 1,6-octanediol (5) and D-glucose (3) using the immobilized beta-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave a mono-beta-glucoside (6) in 61.4% yield, which was converted into the n-hexyl beta-D-glucopyranoside (1) by means of a chemoenzymatic method. The coupling of the n-hexyl beta-D-glucopyranoside congener (13) and 2,3,4-tri-O-acetyl-beta-D-xylosyl congener (14), followed by deprotection, afforded the synthetic n-hexyl O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside (2), which was identical to the natural 2 with respect to the spectral data and specific rotation.
Kishida
Masashi
M
School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba 274-8510, Japan.
Nishiuchi
Miho
M
Kato
Keisuke
K
Akita
Hiroyuki
H
D004800:Enzymes, Immobilized / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*; D014994:Xylose / Q000138:chemical synthesis*; D001617:beta-Glucosidase / Q000737:chemistry
D004800:Enzymes, Immobilized; D009005:Monosaccharides; C496387:n-hexyl beta-D-glucopyranoside; D014994:Xylose; D001617:beta-Glucosidase