A simple method for the small scale synthesis and solid-phase extraction purification of steroid sulfates
Date
2014
Authors
Waller, Christopher C.
McLeod, Malcolm D.
Journal Title
Journal ISSN
Volume Title
Publisher
Elsevier
Abstract
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 1μg of testosterone (17β-hydroxyandrost-4-en-3-one) as monitored by liquid chromatography-mass spectrometry (LCMS).
Description
Keywords
anti-doping, solid-phase extraction, steroid sulfate, sulfate ester, sulfation, magnetic resonance spectroscopy, molecular structure, solid phase extraction, steroids, sulfates
Citation
Collections
Source
Steroids
Type
Journal article
Book Title
Entity type
Access Statement
Open Access