Chemoenzymatic synthesis of sacranosides a and B.
Direct beta-glucosidation between (-)-myrtenol and nerol and D-glucose (3) using the immobilized beta-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave myrtenyl O-beta-D-glucoside (4) and neryl O-beta-D-glucoside (10), respectively. The coupling of the myrtenyl or neryl O-beta-D-glucopyranoside congeners (7 or 13) and 2,3,4-tri-O-benzoyl-beta-L-arabinopyranosyl bromide (8) afforded the coupled products (9 or 14), respectively. Deprotection of the coupled products (9 or 14) afforded the synthetic myrtenyl 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (Sacranoside A, 1) or neryl 6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside (Sacranoside B, 2), respectively.
Kawahara
Eiji
E
School of Pharmaceutical Sciences, Toho University, Funabashi, Chiba, Japan.
Fujii
Mikio
M
Ida
Yoshiteru
Y
Akita
Hiroyuki
H
D002240:Carbohydrate Sequence; D005960:Glucosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D013729:Terpenes / Q000138:chemical synthesis*
D005960:Glucosides; D007202:Indicators and Reagents; D013729:Terpenes; C084878:kenposide A; C044909:pinen-10-yl vicianoside