title: Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4-²H₅]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry.
abstract: The 3- and 21-monosulfates of pentadeuterated 5β-tetrahydrocorticosteroides were synthesized, starting from cortisol and 11-deoxycotisol. The principal reactions used were (1) perdeuteration of the methylene groups adjacent to the 3-oxo group of 17,20:20,21-bismethylendioxy-5β-3-ketosteroids with NaOD in CH(3)OD followed by stereoselective reduction with NaBD(4), (2) sulfation of hydroxy groups with sulfur trioxide-trimethylamine complex, and (3) removal of the 17,20:20,21-bismethylendioxy group with hydrogen fluoride. The labeled compounds can be used as internal standards in liquid chromatography/mass spectrometry assays for clinical and biochemical studies.
authors: Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka 577-8502, Japan. ikegawa@phar.kindai.ac.jp
authors: Shigeo
authors: S
authors: Ikegawa
authors: Kaori
authors: K
authors: Nagae
authors: Takayuki
authors: T
authors: Mabuchi
authors: Rika
authors: R
authors: Okihara
authors: Maki
authors: M
authors: Hasegawa
authors: Toshie
authors: T
authors: Minematsu
authors: Takashi
authors: T
authors: Iida
authors: Kuniko
authors: K
authors: Mitamura
mesh_terms: D000305:Adrenal Cortex Hormones / Q000138:chemical synthesis* / Q000737:chemistry; D002853:Chromatography, Liquid / Q000379:methods; D007664:Ketosteroids / Q000737:chemistry*; D013058:Mass Spectrometry / Q000379:methods; D012015:Reference Standards
chemical_list: D000305:Adrenal Cortex Hormones; D007664:Ketosteroids