Abstract：
:The accurate analysis of trace components in complex biological matrices requires the use of reliable internal standards. For liquid chromatography/mass spectrometry analysis, the stable isotope-labeled analogues of the analyte molecules are the most appropriate internal standards. In this paper the synthesis of the 3- and 21-monosulfates of allo-tetrahydrocorticosteroids labeled with four or five deuterium atoms is described. The principal reactions used were (1) hydrogen-deuterium exchange reaction of active methylene groups adjacent to 3- and 11-oxo group of 17,20;20,21-bismethylenedioxy derivatives of 5α-3-ketosteroids and/or 5α-11-ketosteroids with NaOD in CH(3)OD followed by reduction with NaBD(4), (2) epimerization of the 3β-hydroxy group into a 3α configuration, (3) sulfation of hydroxy groups at C-3 or C-21 in the resulting substrates with sulfur trioxide-trimethylamine complex, and (4) removal of 17,20;20,21-bismethylenedioxy groups with hydrogen fluoride in ethanol. Isotopic purity was found to be satisfactory by MS, and NMR properties of the new compounds were tabulated. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies.
journal_name
Steroidsjournal_title
Steroidsauthors
Mitamura K,Mabuchi T,Nagae K,Nakajima M,Matsumoto R,Fujioka S,Sato K,Satoh née Okihara R,Iida T,Ogawa S,Hofmann AF,Ikegawa Sdoi
10.1016/j.steroids.2012.08.007subject
Has Abstractpub_date
2012-11-01 00:00:00pages
1423-37issue
13eissn
0039-128Xissn
1878-5867pii
S0039-128X(12)00235-8journal_volume
77pub_type
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