title: Chemoenzymatic synthesis of n-hexyl and O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranosides.
abstract: 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.
authors.affiliation: School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba 274-8510, Japan.
authors.forename: Masashi
authors.initials: M
authors.lastname: Kishida
authors.forename: Miho
authors.initials: M
authors.lastname: Nishiuchi
authors.forename: Keisuke
authors.initials: K
authors.lastname: Kato
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Akita
mesh_terms: D004800:Enzymes, Immobilized / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*; D014994:Xylose / Q000138:chemical synthesis*; D001617:beta-Glucosidase / Q000737:chemistry
chemical_list: D004800:Enzymes, Immobilized; D009005:Monosaccharides; C496387:n-hexyl beta-D-glucopyranoside; D014994:Xylose; D001617:beta-Glucosidase