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Synthesis of 1β‐hydroxydeoxycholic acid in H‐2 and unlabeled forms
Author(s) -
Hayes Martin A.,
Roberts Ieuan,
Grönberg Gunnar,
Lv Kexin,
Lin Baorui,
Bergare Jonas,
Elmore Charles S.
Publication year - 2017
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3495
Subject(s) - chemistry , deoxycholic acid , yield (engineering) , deuterium , combinatorial chemistry , bile acid , organic chemistry , stereochemistry , biochemistry , materials science , physics , quantum mechanics , metallurgy
1β–hydroxydeoxycholic acid in unlabeled and stable isotope labeled forms was required for use as a biomarker for Cytochrome P450 3A4/5 activity. A lengthy synthesis was undertaken to deliver the unlabeled compound and in the process, to develop a route to the deuterium labeled compound. The synthesis of the unlabeled compound was completed but in a very low yield. Concurrent with the synthetic approach, a biosynthetic route was pursued and this approach proved to be much more rapid and afforded the compound in both unlabeled and deuterium labeled forms in a 1‐step oxidation from deoxycholic acid and [D 4 ]deoxycholic acid, respectively.