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.
MeSH terms
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Acetylglucosaminidase / metabolism
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Cadmium / chemistry
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Carbonates / chemistry
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Estradiol / analogs & derivatives*
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Estradiol / chemical synthesis
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Estriol / analogs & derivatives*
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Estriol / chemical synthesis
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Estrone / analogs & derivatives*
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Estrone / chemical synthesis
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Fabaceae / enzymology
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Glucosamine / analogs & derivatives*
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Glucosamine / chemical synthesis
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Hydrogen-Ion Concentration
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Hydrolysis
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Hydroxides
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Magnetic Resonance Spectroscopy
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Methanol
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Molecular Structure
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Plants, Medicinal
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Potassium Compounds
Substances
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3,16,17-trihydroxyestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside
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3,17-dihydroxyestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside
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3-hydroxy-17--oxoestra-1,3,5(10)-trien-15-yl-2'-acetamido-2'-deoxyglucopyranoside
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Carbonates
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Hydroxides
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Potassium Compounds
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Cadmium
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Estrone
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Estradiol
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cadmium carbonate
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Acetylglucosaminidase
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Estriol
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Glucosamine
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potassium hydroxide
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Methanol