Issue 47, 2014

Glucuronidation of bile acids under flow conditions: design of experiments and Koenigs–Knorr reaction optimization

Abstract

An efficient method for the C3-glucuronidation of bile acids is developed under flow conditions. A modular mesoreactor assisted flow set-up was combined with statistical design of experiments to speed up the optimization of the Koenigs–Knorr reaction in terms of yield, regioselectivity, costs, as well as technical and practical standpoints. Using the optimal conditions, selective glucuronidation of naturally occurring bile acids was successfully achieved offering a new, valuable route to C3-glucuronidated bile acids useful for biological, diagnostic and PK/ADMET investigations.

Graphical abstract: Glucuronidation of bile acids under flow conditions: design of experiments and Koenigs–Knorr reaction optimization

Supplementary files

Article information

Article type
Paper
Submitted
09 Sep 2014
Accepted
26 Sep 2014
First published
26 Sep 2014

Org. Biomol. Chem., 2014,12, 9592-9600

Glucuronidation of bile acids under flow conditions: design of experiments and Koenigs–Knorr reaction optimization

S. Mostarda, P. Filipponi, R. Sardella, F. Venturoni, B. Natalini, R. Pellicciari and A. Gioiello, Org. Biomol. Chem., 2014, 12, 9592 DOI: 10.1039/C4OB01911C

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