A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives
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 method...
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Frontiers Media S.A.
2021-12-01
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| Series: | Frontiers in Molecular Biosciences |
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fmolb.2021.776900/full |
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| author | Jaber A. Alshehri Daniel M. Gill Alan M. Jones |
| author_facet | Jaber A. Alshehri Daniel M. Gill Alan M. Jones |
| author_sort | Jaber A. Alshehri |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d7244f097cb046fa88242d70e5fac665 |
| institution | Kabale University |
| issn | 2296-889X |
| language | English |
| publishDate | 2021-12-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Molecular Biosciences |
| spelling | doaj-art-d7244f097cb046fa88242d70e5fac6652025-01-28T14:30:43ZengFrontiers Media S.A.Frontiers in Molecular Biosciences2296-889X2021-12-01810.3389/fmolb.2021.776900776900A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled DerivativesJaber A. AlshehriDaniel M. GillAlan M. JonesThe 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.https://www.frontiersin.org/articles/10.3389/fmolb.2021.776900/fullsulfationselectivityisotopic labellingsulfuryl transferTBSAB |
| spellingShingle | Jaber A. Alshehri Daniel M. Gill Alan M. Jones A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives Frontiers in Molecular Biosciences sulfation selectivity isotopic labelling sulfuryl transfer TBSAB |
| title | A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives |
| title_full | A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives |
| title_fullStr | A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives |
| title_full_unstemmed | A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives |
| title_short | A Sulfuryl Group Transfer Strategy to Selectively Prepare Sulfated Steroids and Isotopically Labelled Derivatives |
| title_sort | sulfuryl group transfer strategy to selectively prepare sulfated steroids and isotopically labelled derivatives |
| topic | sulfation selectivity isotopic labelling sulfuryl transfer TBSAB |
| url | https://www.frontiersin.org/articles/10.3389/fmolb.2021.776900/full |
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