New cholic acid derivatives: Biocatalytic synthesis and molecular docking study

•Cholic acid esters, mono- and diacetyl derivatives were prepared by biocatalysis.•The influence of various parameters on the enzymatic reactions was studied.•Mild reaction conditions compatible to the environment were applied.•Molecular docking was applied to explain cholic acid behavior.

A series of cholic acid derivatives was synthesized by enzyme catalysis. Eleven acetyl and ester derivatives of cholic acid, eight of them new compounds, were obtained through regioselective lipase-catalyzed reactions in very good to excellent yield. The influence of various reaction parameters in the enzymatic esterification, acetylation and alcoholysis reactions, such as enzyme source, alcohol or acylating agent: substrate ratio, enzyme: substrate ratio, solvent and temperature, was studied. Moreover, in order to shed light to cholic acid behavior in the enzymatic reactions, molecular docking of the lipase with cholic acid and some derivatives was carried out.

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