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Organic & Biomolecular Chemistry

An international journal for the quickest publication of high-quality research covering the breadth of synthetic, physical and biomolecular organic chemistry.




Paper

Org. Biomol. Chem., 2006, 4, 3951 - 3959, DOI: 10.1039/b610499a


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

Natasha L. Hungerford, Andrew R. McKinney, Allen M. Stenhouse and Malcolm D. McLeod


The temporary protection of 17-alkyl-5-androstane-3,16,17 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 image for this article  (ID: b610499a)