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

Jaber Alshehri, Daniel Gill, Alan M Jones

Research output: Contribution to journalArticlepeer-review

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 languageEnglish
Article number776900
JournalFrontiers in Molecular Bioscience
Volume8
DOIs
Publication statusPublished - 24 Dec 2021

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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