Synthesis of 1β‐hydroxydeoxycholic acid in H‐2 and unlabeled forms

Abstract

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 ]deoxycholic acid, respectively.

Continuum of Host-Gut Microbial Co-metabolism: Host CYP3A4/3A7 are Responsible for Tertiary Oxidations of Deoxycholate Species

“…Synthesis of DCA-1b-ol. We synthesized 1b, 3a, 12a-trihydroxy-5b-cholan-24-oic acid (DCA-1b-ol, CAS 80434-32-8) from DCA according to the same procedure described in Hayes et al (2017). The LC-MS/MS and NMR data of DCA-1b-ol were summarized in Supplemental Fig.…”