Synthesis of 19-hydroxy-[7-2H2]androstenedione for human metabolism studies.
19-Hydroxyandrostenedione (19-OHA), highly labeled with deuterium at position 7, was synthesized from unlabeled androstenediol diacetate. The deuterium labels were introduced into the 7-keto compound with dichloroaluminum deuteride to obtain [7-2H2]androstenediol. The labeled androstenediol diacetate was converted to the labeled 19-OHA by a five-step sequence without appreciable loss of deuterium. The labeled 19-OHA is useful as an internal standard for gas chromatography-mass spectroscopy analysis of the endogenous levels and as a tracer for in vivo metabolic studies.
Ohnishi
S
S
Endocrine Biochemistry Department, Medical Foundation of Buffalo, New York 14203-1196.
Kosaki
T
T
Osawa
Y
Y
D015114:Androstenediol; D000735:Androstenedione / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D003903:Deuterium; D005260:Female; D006801:Humans; D011247:Pregnancy
D000735:Androstenedione; D015114:Androstenediol; C011482:19-hydroxy-4-androstene-3,17-dione; D003903:Deuterium