Synthesis of 2-hydroxyestriol monoglucuronides and monosulfates.
The ring A monoglucuronides and monosulfates of 2-hydroxyestriol were synthesized from 2-hydroxyestriol 16,17-diacetate by means of the Koenigs-Knorr reaction with methyl alpha-acetobromoglucuronate and sulfation with sulfur trioxide-pyridine complex, respectively. The conjugated positions of these compounds were definitely established by conversion to 2-hydroxyestriol monomethyl ethers by methylation, then enzymatic hydrolysis. The ring D monoglucuronides and monosulfates of 2-hydroxyestriol were also prepared from 2-hydroxyestriol 2,3-dibenzyl ether by glucuronidation and sulfation in a similar fashion followed by debenzylation, respectively. The positions of conjugation were established on the basis of their 1H-nuclear magnetic resonance spectral data.
Ohkubo
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Pharmaceutical Institute, Tohoku University, Sendai, Japan.
Wakasawa
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Nambara
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D000818:Animals; D004964:Estriol / Q000138:chemical synthesis / Q000031:analogs & derivatives; D005965:Glucuronates / Q000138:chemical synthesis; D005966:Glucuronidase / Q000378:metabolism; D006372:Helix, Snails / Q000201:enzymology; D013429:Sulfatases / Q000378:metabolism; D013464:Sulfuric Acids / Q000138:chemical synthesis
D005965:Glucuronates; D013464:Sulfuric Acids; C008012:2-hydroxyestriol; D013429:Sulfatases; D005966:Glucuronidase; D004964:Estriol