An investigation of the reactions involved in the chemical synthesis of estrogen glucosiduronates was undertaken to establish conditions for the synthesis of the doubly labeled conjugates. The α- and β-anomers of methyl 1,2,3,4-tetra-0-acetyl-D-glucuronate were prepared from glucuronolactone by base and acid catalyzed acetylations respectively. Bromination of either of these compounds yielded methyl 2,3,4-tri-0-acetyl-1-bromo-1-deoxy-α-D-glucuronate. Estrone was converted by a series of reactions to 3,16α-diacetoxy-17-keto-estra-1,3,5(10)-triene. Attempted reduction of the 17-keto group was unsuccessful, and for this reason estriol-17β-glucosiduronate could not be prepared. Estradiol glucosiduronates could not be obtained in crystalline form in significant yields. Estrone was successfully conjugated with methyl 2,3,4-tri-0-acetyl-1-bromo-1-deoxy-α-D-glucuronate. Deacetylation under alkaline conditions gave a solid compound presumed to be estrone glucosiduronate. / Medicine, Faculty of / Biochemistry and Molecular Biology, Department of / Graduate
| Identifer | oai:union.ndltd.org:UBC/oai:circle.library.ubc.ca:2429/39791 |
| Date | January 1964 |
| Creators | Roy, Joan Elaine |
| Publisher | University of British Columbia |
| Source Sets | University of British Columbia |
| Language | English |
| Detected Language | English |
| Type | Text, Thesis/Dissertation |
| Rights | For non-commercial purposes only, such as research, private study and education. Additional conditions apply, see Terms of Use https://open.library.ubc.ca/terms_of_use. |
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