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

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

Department of Structural Biology

Indiana University Bloomington
United States Food and Drug Administration
Hauptman-Woodward Medical Research Institute, Inc.

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

The α- and β-anomers of the 17β-d-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl₄-promoted reaction between β-acetoxy GAM and the t-17β-hydroxyl group of EE₂-3-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.

Original language	English
Pages (from-to)	81-87
Number of pages	7
Journal	Journal of Steroid Biochemistry
Volume	18
Issue number	1
DOIs	https://doi.org/10.1016/0022-4731(83)90334-5
State	Published - Jan 1983

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title = "Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol",

abstract = "The α- and β-anomers of the 17β-d-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl4-promoted reaction between β-acetoxy GAM and the t-17β-hydroxyl group of EE2-3-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.",

author = "Hadd, \{Harry E.\} and William Slikker and Miller, \{Dwight W.\} and Helton, \{Edward D.\} and Duax, \{William L.\} and Strong, \{Phyllis D.\} and Swenson, \{Dale C.\}",

year = "1983",

month = jan,

doi = "10.1016/0022-4731(83)90334-5",

language = "English",

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TY - JOUR

T1 - Synthesis and characterization of the anomeric pair of 17β-glucuronides of ethynylestradiol

AU - Hadd, Harry E.

AU - Slikker, William

AU - Miller, Dwight W.

AU - Helton, Edward D.

AU - Duax, William L.

AU - Strong, Phyllis D.

AU - Swenson, Dale C.

PY - 1983/1

Y1 - 1983/1

N2 - The α- and β-anomers of the 17β-d-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl4-promoted reaction between β-acetoxy GAM and the t-17β-hydroxyl group of EE2-3-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.

AB - The α- and β-anomers of the 17β-d-glucuronide conjugate of ethynylestradiol were synthesized by the SnCl4-promoted reaction between β-acetoxy GAM and the t-17β-hydroxyl group of EE2-3-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.

UR - https://www.scopus.com/pages/publications/0020662721

U2 - 10.1016/0022-4731(83)90334-5

DO - 10.1016/0022-4731(83)90334-5

M3 - Article

C2 - 6865406

AN - SCOPUS:0020662721

SN - 0022-4731

VL - 18

SP - 81

EP - 87

JO - Journal of Steroid Biochemistry

JF - Journal of Steroid Biochemistry

IS - 1

ER -

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

Abstract

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