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 | Zendy

Natasha L. Hungerford | Zendy; Andrew R. McKinney | Zendy; Allen M. Stenhouse | Zendy; Malcolm D. McLeod | Zendy

Open Access

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

Author(s) -

Natasha L. Hungerford,

Andrew R. McKinney,

Allen M. Stenhouse,

Malcolm D. McLeod

Publication year - 2006

Publication title -

organic and biomolecular chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.923

H-Index - 146

eISSN - 1477-0539

pISSN - 1477-0520

DOI - 10.1039/b610499a

Subject(s) - steroid , chemistry , conjugate , combinatorial chemistry , sulfate , organic chemistry , stereochemistry , biochemistry , hormone , mathematical analysis , mathematics

The temporary protection of 17alpha-alkyl-5alpha-androstane-3beta,16beta,17beta 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.

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