کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
2027579 | 1542715 | 2014 | 7 صفحه PDF | دانلود رایگان |
• A simple small scale synthesis and purification of steroid sulfates is reported.
• Suitable for adoption by laboratories with limited chemical synthesis expertise.
• Milligram–microgram scale preparation of 16 examples with 65 to >98% conversion.
• High purity achieved by a rapid single step solid-phase extraction purification.
• Procedures, characterization data, NMR and mass spectra provided for all compounds.
Steroid sulfates are a major class of steroid metabolite that are of growing importance in fields such as anti-doping analysis, the detection of residues in agricultural produce or medicine. Despite this, many steroid sulfate reference materials may have limited or no availability hampering the development of analytical methods. We report simple protocols for the rapid synthesis and purification of steroid sulfates that are suitable for adoption by analytical laboratories. Central to this approach is the use of solid-phase extraction (SPE) for purification, a technique routinely used for sample preparation in analytical laboratories around the world. The sulfate conjugates of sixteen steroid compounds encompassing a wide range of steroid substitution patterns and configurations are prepared, including the previously unreported sulfate conjugates of the designer steroids furazadrol (17β-hydroxyandrostan[2,3-d]isoxazole), isofurazadrol (17β-hydroxyandrostan[3,2-c]isoxazole) and trenazone (17β-hydroxyestra-4,9-dien-3-one). Structural characterization data, together with NMR and mass spectra are reported for all steroid sulfates, often for the first time. The scope of this approach for small scale synthesis is highlighted by the sulfation of 1 μg of testosterone (17β-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography–mass spectrometry (LCMS).
Figure optionsDownload as PowerPoint slide
Journal: Steroids - Volume 92, 15 December 2014, Pages 74–80