title: Synthesis of 15 alpha-hydroxyestrogen 15-N-acetylglucosaminides.
abstract: The synthesis of 15-N-acetylglucosaminides of 15 alpha-hydroxyesterone, 15 alpha-hydroxyestradiol, and 15 alpha-hydroxyestriol (estetrol) is described. The latter two were prepared by condensation of 2-acetamido-1 alpha-chloro-1,2-dideoxy-3,4,6-trio-O-acetyl-D-glucopyranose with appropriately protected 15 alpha-hydroxyestrogens by the Koenigs-Knorr reaction employing cadmium carbonate as a catalyst. Subsequent removal of protecting groups with methanolic potassium hydroxide provided the desired conjugates. 15 alpha-Hydroxyestrone 15-N-acetylglucosaminide was synthesized from the corresponding 15 alpha-hydroxyestradiol derivative by Jones oxidation followed by brief alkaline hydrolysis. These conjugates underwent enzymatic hydrolysis with beta-N-acetylglucosaminidase from Jack beans to produce 15 alpha-hydroxyestrogens.
authors.affiliation: Hatano Research Institute, Food and Drug Safety Center, Kanagawa, Japan.
authors.forename: E
authors.initials: E
authors.lastname: Suzuki
authors.forename: S
authors.initials: S
authors.lastname: Namba
authors.forename: H
authors.initials: H
authors.lastname: Kurihara
authors.forename: J
authors.initials: J
authors.lastname: Goto
authors.forename: Y
authors.initials: Y
authors.lastname: Matsuki
authors.forename: T
authors.initials: T
authors.lastname: Nambara
mesh_terms: D000118:Acetylglucosaminidase / Q000378:metabolism; D002104:Cadmium / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004964:Estriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004970:Estrone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007887:Fabaceae / Q000201:enzymology; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D006878:Hydroxides; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol; D015394:Molecular Structure; D010946:Plants, Medicinal; D017680:Potassium Compounds
chemical_list: C094250:3,16,17-trihydroxyestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside; C094251:3,17-dihydroxyestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside; C094252:3-hydroxy-17--oxoestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside; D002254:Carbonates; D006878:Hydroxides; D017680:Potassium Compounds; D002104:Cadmium; D004970:Estrone; D004958:Estradiol; C038075:cadmium carbonate; D000118:Acetylglucosaminidase; D004964:Estriol; D005944:Glucosamine; C029943:potassium hydroxide; D000432:Methanol