Chemoenzymatic Synthesis of Sacranosides A and B

• Published in: Chemical & Pharmaceutical Bulletin Vol. 54; no. 3; pp. 387 - 390
• Main Authors: Kawahara, Eiji, Fujii, Mikio, Ida, Yoshiteru, Akita, Hiroyuki
• Format: Journal Article
• Language: English; Japanese
• Published: TOKYO The Pharmaceutical Society of Japan 01.03.2006; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Carbohydrate Sequence; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Glucosides - chemical synthesis; Indicators and Reagents; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Sequence Data; natural product synthesis; Pharmacology & Pharmacy; Physical Sciences; Sacranoside; Science & Technology; Terpenes - chemical synthesis; β-glucosidase; β-glucosidation; RHODIOLA-SACRA; Sacranoside; RADIX; beta-glucosidation; INHIBITORS; MEDICINES; UNDERGROUND PART; beta-glucosidase; natural product synthesis; CONSTITUENTS
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.54.387

Direct β-glucosidation between (−)-myrtenol and nerol and D-glucose (3) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave myrtenyl O-β-D-glucoside (4) and neryl O-β-D-glucoside (10), respectively. The coupling of the myrtenyl or neryl O-β-D-glucopyranoside congeners (7 or 13) and 2,3,4-tri-O-benzoyl-β-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-α-L-arabinopyranosyl-β-D-glucopyranoside (Sacranoside A, 1) or neryl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside (Sacranoside B, 2), respectively.