title: 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.
authors.affiliation: Laboratory of Medicinal and Advanced Synthetic Chemistry (Lab MASC), Department of Pharmaceutical Sciences, University of Perugia, Via del Liceo 1, I-06123 Perugia, Italy. antimo.gioiello@unipg.it.
authors.forename: Serena
authors.initials: S
authors.lastname: Mostarda
authors.forename: Paolo
authors.initials: P
authors.lastname: Filipponi
authors.forename: Roccaldo
authors.initials: R
authors.lastname: Sardella
authors.forename: Francesco
authors.initials: F
authors.lastname: Venturoni
authors.forename: Benedetto
authors.initials: B
authors.lastname: Natalini
authors.forename: Roberto
authors.initials: R
authors.lastname: Pellicciari
authors.forename: Antimo
authors.initials: A
authors.lastname: Gioiello
mesh_terms: D001647:Bile Acids and Salts / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000295:instrumentation; D004867:Equipment Design; D020719:Glucuronides / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001647:Bile Acids and Salts; D020719:Glucuronides