A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives

Jaber Alshehri; Daniel Gill; Alan M Jones

doi:10.3389/fmolb.2021.776900

A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives

Jaber Alshehri, Daniel Gill, Alan M Jones

Pharmacy

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Abstract

The treatment of common steroids: estrone, estradiol, cortisol, and pregnenolone with tributylsulfoammonium betaine (TBSAB) provides a convenient chemoselective conversion of the steroids alcohol/phenol moiety to the corresponding steroidal organosulfate. An important feature of the disclosed methodology is the millimolar scale of the reaction, and the isolation of the corresponding steroid sulfates as their biologically relevant sodium salts without the need for ion-exchange chromatography. The scope of the method was further explored in the estradiol and pregnanediol steroid systems with the bis-sulfated derivatives. Ultimately, a method to install an isotopic label, deuterium (²H) combined with estrone sulfation is a valuable tool for its mass-spectrometric quantification in biological studies.

Original language	English
Article number	776900
Journal	Frontiers in Molecular Bioscience
Volume	8
DOIs	https://doi.org/10.3389/fmolb.2021.776900 https://doi.org/10.3389/fmolb.2021.776900
Publication status	Published - 24 Dec 2021

Bibliographical note

Funding Information:
The authors thank the above funding bodies for supporting our research programme. The authors thank Louise Male for X-ray crystallography, Allen Bowden for HPLC analysis, Chris Williams for mass-spectroscopic studies, and Cecile Le Duff for NMR assistance. Requests for milligram samples will be considered by the authors until samples are exhausted.

Keywords

Sulfation
Selectivity
isotopic labelling
Sulfuryl transfer
TBSAB

ASJC Scopus subject areas

Biochemistry
Biochemistry, Genetics and Molecular Biology (miscellaneous)
Molecular Biology

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alshehrij2021sulfurylFinal published version, 1.32 MBLicence: Creative Commons: Attribution (CC BY)

Data accompanying the paper "A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives"
Jones, A. (Creator), University of Birmingham, 17 Sept 2021
DOI: https://doi.org/10.25500/edata.bham.00000720
Dataset

Cite this

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title = "A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives",

abstract = "The treatment of common steroids: estrone, estradiol, cortisol, and pregnenolone with tributylsulfoammonium betaine (TBSAB) provides a convenient chemoselective conversion of the steroids alcohol/phenol moiety to the corresponding steroidal organosulfate. An important feature of the disclosed methodology is the millimolar scale of the reaction, and the isolation of the corresponding steroid sulfates as their biologically relevant sodium salts without the need for ion-exchange chromatography. The scope of the method was further explored in the estradiol and pregnanediol steroid systems with the bis-sulfated derivatives. Ultimately, a method to install an isotopic label, deuterium (2H) combined with estrone sulfation is a valuable tool for its mass-spectrometric quantification in biological studies. ",

keywords = "Sulfation, Selectivity, isotopic labelling, Sulfuryl transfer, TBSAB",

author = "Jaber Alshehri and Daniel Gill and Jones, {Alan M}",

note = "Funding Information: The authors thank the above funding bodies for supporting our research programme. The authors thank Louise Male for X-ray crystallography, Allen Bowden for HPLC analysis, Chris Williams for mass-spectroscopic studies, and Cecile Le Duff for NMR assistance. Requests for milligram samples will be considered by the authors until samples are exhausted.",

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AU - Alshehri, Jaber

AU - Gill, Daniel

AU - Jones, Alan M

N1 - Funding Information: The authors thank the above funding bodies for supporting our research programme. The authors thank Louise Male for X-ray crystallography, Allen Bowden for HPLC analysis, Chris Williams for mass-spectroscopic studies, and Cecile Le Duff for NMR assistance. Requests for milligram samples will be considered by the authors until samples are exhausted.

PY - 2021/12/24

Y1 - 2021/12/24

N2 - The treatment of common steroids: estrone, estradiol, cortisol, and pregnenolone with tributylsulfoammonium betaine (TBSAB) provides a convenient chemoselective conversion of the steroids alcohol/phenol moiety to the corresponding steroidal organosulfate. An important feature of the disclosed methodology is the millimolar scale of the reaction, and the isolation of the corresponding steroid sulfates as their biologically relevant sodium salts without the need for ion-exchange chromatography. The scope of the method was further explored in the estradiol and pregnanediol steroid systems with the bis-sulfated derivatives. Ultimately, a method to install an isotopic label, deuterium (2H) combined with estrone sulfation is a valuable tool for its mass-spectrometric quantification in biological studies.

AB - The treatment of common steroids: estrone, estradiol, cortisol, and pregnenolone with tributylsulfoammonium betaine (TBSAB) provides a convenient chemoselective conversion of the steroids alcohol/phenol moiety to the corresponding steroidal organosulfate. An important feature of the disclosed methodology is the millimolar scale of the reaction, and the isolation of the corresponding steroid sulfates as their biologically relevant sodium salts without the need for ion-exchange chromatography. The scope of the method was further explored in the estradiol and pregnanediol steroid systems with the bis-sulfated derivatives. Ultimately, a method to install an isotopic label, deuterium (2H) combined with estrone sulfation is a valuable tool for its mass-spectrometric quantification in biological studies.

KW - Sulfation

KW - Selectivity

KW - isotopic labelling

KW - Sulfuryl transfer

KW - TBSAB

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JO - Frontiers in Molecular Bioscience

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ER -

A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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Datasets

Data accompanying the paper "A sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives"

Cite this