Synthesis of deuterium-labeled 5 alpha-androstane-3 alpha, 17 beta-diol and its 17 beta-glucuronide.
Using unlabeled androsterone as starting material, 5 alpha-[16,16-2H2]androstan-3 alpha-ol-17-one was synthesized by exchange using deuterated potassium methoxide. This labeled androsterone product was reduced by sodium borodeuteride, which gave predominantly trideuterated 5 alpha-androstane-3 alpha, 17 beta-diol. The labeled androstanediol was conjugated with glucuronide by using the Koenig-Knorr reaction with methyl-1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranosuronate . The dominant product was identified by thermospray high-performance liquid chromatography/mass spectrometry (MS) and electrospray MS as 5 alpha-[16,16,17-2H3]androstane-3 alpha, 17 beta-diol, 17 beta-glucuronide.
Chung
B C
BC
Children's Hospital Oakland Research Institute, California 94609.
Mallamo
J P
JP
Juniewicz
P E
PE
Shackleton
C H
CH
D015113:Androstane-3,17-diol / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003903:Deuterium; D005965:Glucuronates / Q000138:chemical synthesis*; D007553:Isotope Labeling; D013058:Mass Spectrometry
D005965:Glucuronates; D015113:Androstane-3,17-diol; D003903:Deuterium