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  1. Article ; Online: Synthesis of the Alkylsulfonate Metabolites Cysteinolic Acid, 3-Amino-2-hydroxypropanesulfonate, and 2,3-Dihydroxypropanesulfonate.

    Burchill, Laura / Zudich, Luca / van der Peet, Phillip L / White, Jonathan M / Williams, Spencer J

    The Journal of organic chemistry

    2022  Volume 87, Issue 6, Page(s) 4333–4342

    Abstract: Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH) ...

    Abstract Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH)
    MeSH term(s) Bile Acids and Salts ; Chenodeoxycholic Acid/metabolism ; Cysteine/analogs & derivatives ; Epichlorohydrin
    Chemical Substances Bile Acids and Salts ; Epichlorohydrin (08OOR508C0) ; Chenodeoxycholic Acid (0GEI24LG0J) ; cysteinolic acid (16421-58-2) ; Cysteine (K848JZ4886)
    Language English
    Publishing date 2022-02-24
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c00036
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Synthesis of the Alkylsulfonate Metabolites Cysteinolic Acid, 3-Amino-2-hydroxypropanesulfonate, and 2,3-Dihydroxypropanesulfonate

    Burchill, Laura / Zudich, Luca / van der Peet, Phillip L. / White, Jonathan M. / Williams, Spencer J.

    Journal of organic chemistry. 2022 Feb. 24, v. 87, no. 6

    2022  

    Abstract: Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH)₂ and (Boc-l-Cys-OH)₂, respectively), R- and S-3- ... ...

    Abstract Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH)₂ and (Boc-l-Cys-OH)₂, respectively), R- and S-3-amino-2-hydroxypropanesulfonate (from S- and R-epichlorohydrin, respectively), and R- and S-2,3-dihydroxypropanesulfonate (from S- and R-epichlorohydrin, respectively). d-Cysteinolate bile salts were generated by coupling with cholic and chenodeoxycholic acids. A series of single-crystal 3D X-ray structures confirmed the absolute configurations of the aminosulfonates. By comparison of optical rotation, we assign naturally occurring 3-amino-2-hydroxypropanesulfonate from Gateloupia livida as possessing the R-configuration. This simple synthetic approach will support future studies of the occurrence, chemotaxonomic distribution, and metabolism of these alkylsulfonates.
    Keywords X-radiation ; bile ; chemotaxonomy ; metabolism ; metabolites ; organic chemistry
    Language English
    Dates of publication 2022-0224
    Size p. 4333-4342.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c00036
    Database NAL-Catalogue (AGRICOLA)

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