Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol

Harry E. Hadd; William Slikker; Dwight W. Miller; Edward D. Helton; William L. Duax; Phyllis D. Strong; Dale C. Swenson

doi:10.1016/0022-4731(83)90334-5

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Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol

Journal article

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Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol

Harry E. Hadd, William Slikker, Dwight W. Miller, Edward D. Helton, William L. Duax, Phyllis D. Strong and Dale C. Swenson

Journal of steroid biochemistry, Vol.18(1), pp.81-87

1983

DOI: 10.1016/0022-4731(83)90334-5

PMID: 6865406

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Abstract

The α- and β-anomers of the 17β- d-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl 4-promoted reaction between β-acetoxy GAM and the t-17β-hydroxyl group of EE 2-3-acetate. The conjugates were resolved by crystallization and HPLC. Positive identification was established by u.v. spectrophotometry, i.r. and mass spectrometry and 1H- and 134C-n.m.r. The structure of the β-anomer was confirmed by X-ray crystallographic analysis. In addition, the α-anomer was refractory to hydrolysis by bovine β-glucuronidase, establishing a biochemical difference between the conjugate pair.

Details

Title: Subtitle: Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol
Creators: Harry E. Hadd - Indiana University School of Medicine
William Slikker - Department of Health and Human Services, Food and Drug Administration, National Center for Toxicological Research, Jefferson, AR 72079 U.S.A
Dwight W. Miller - Department of Health and Human Services, Food and Drug Administration, National Center for Toxicological Research, Jefferson, AR 72079 U.S.A
Edward D. Helton - Department of Health and Human Services, Food and Drug Administration, National Center for Toxicological Research, Jefferson, AR 72079 U.S.A
William L. Duax - Medical Foundation of Buffalo, Buffalo, 14203, U.S.A
Phyllis D. Strong - Medical Foundation of Buffalo, Buffalo, 14203, U.S.A
Dale C. Swenson - Medical Foundation of Buffalo, Buffalo, 14203, U.S.A
Resource Type: Journal article
Publication Details: Journal of steroid biochemistry, Vol.18(1), pp.81-87
Publisher: Elsevier B.V
DOI: 10.1016/0022-4731(83)90334-5
PMID: 6865406
ISSN: 0022-4731
eISSN: 1879-1220
Language: English
Date published: 1983
Academic Unit: Chemistry
Record Identifier: 9984622044402771

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