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Issue 21, 2006
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Selective manipulation of steroid hydroxyl groups with boronate esters: efficient access to antigenic C-3 linked steroid–protein conjugates and steroid sulfate standards for drug detection

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Abstract

The temporary protection of 17α-alkyl-5α-androstane-3β,16β,17β triols as boronate esters is an efficient method for their regioselective functionalisation. This has been applied to the synthesis of protein–steroid conjugates 7–10 suitable for the development of immunoassays targeting classes of steroids banned from competition in Australian horse racing and other sports. The synthesis of steroids sulfate conjugates 42 and 44 for use as reference standards is also reported.

Graphical abstract: Selective manipulation of steroid hydroxyl groups with boronate esters: efficient access to antigenic C-3 linked steroid–protein conjugates and steroid sulfate standards for drug detection

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Publication details

The article was received on 02 Aug 2006, accepted on 13 Sep 2006 and first published on 22 Sep 2006


Article type: Paper
DOI: 10.1039/B610499A
Org. Biomol. Chem., 2006,4, 3951-3959

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    Selective manipulation of steroid hydroxyl groups with boronate esters: efficient access to antigenic C-3 linked steroid–protein conjugates and steroid sulfate standards for drug detection

    N. L. Hungerford, A. R. McKinney, A. M. Stenhouse and M. D. McLeod, Org. Biomol. Chem., 2006, 4, 3951
    DOI: 10.1039/B610499A

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