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. 2021 Dec 24:8:776900.
doi: 10.3389/fmolb.2021.776900. eCollection 2021.

A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives

Jaber A Alshehri  1 , Daniel M Gill  1 , Alan M Jones  1
Affiliations

A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives

Jaber A Alshehri et al. Front Mol Biosci. .

Erratum in

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: TBSAB; isotopic labelling; selectivity; sulfation; sulfuryl transfer.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.

Figures

CHART 1
CHART 1
Current approaches to steroid sulfation and this work using TBSAB.
SCHEME 1
SCHEME 1
TBSAB mediated regioselective sulfation of β-estradiol (1) affords the mono- or double sulfated estradiols as their sodium salts.
SCHEME 2
SCHEME 2
Sulfation of the pregnenolone (6) and pregnendiol (9) steroids.
SCHEME 3
SCHEME 3
Regioselective C (21) sulfate ester formation on cortisol (12).
SCHEME 4
SCHEME 4
Estrone and estrone-d2 sulfation using TBSAB.
FIGURE 1
FIGURE 1
Overlay of 1H NMR spectra of estrone (blue, 15) and estrone-d2 (red, 18) shows the diagnostic reduction of the diastereotopic C (16) protons.
See this image and copyright information in PMC

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References

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