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; Malcolm D. McLeod

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, Malcolm D. McLeod^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3951-3959
Number of pages	9
Journal	Organic and Biomolecular Chemistry
Volume	4
Issue number	21
DOIs	https://doi.org/10.1039/b610499a
Publication status	Published - 2006
Externally published	Yes

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10.1039/b610499a

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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.",

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publisher = "Royal Society of Chemistry",

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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. / Hungerford, Natasha L.; McKinney, Andrew R.; Stenhouse, Allen M. et al.
In: Organic and Biomolecular Chemistry, Vol. 4, No. 21, 2006, p. 3951-3959.

Research output: Contribution to journal › Article › peer-review

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T1 - Selective manipulation of steroid hydroxyl groups with boronate esters

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AU - Stenhouse, Allen M.

AU - McLeod, Malcolm D.

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AB - 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.

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JF - Organic and Biomolecular Chemistry

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ER -

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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