An Accessible Continuous Flow Procedure for the Enantioselective Desymmetrization of a Key Precursor of Bioactive Myo ‐Inositol Derivatives
Year: 2025
Type: article
Abstract: We report herein continuous flow conditions for the TL‐IM lipase‐catalyzed enantioselective desymmetrization of 4,6‐di‐ O ‐benzyl‐ myo ‐inositol, a relevant precursor of bioactive myo ‐inositol derivatives to the D‐1‐ O ‐acetyl derivative. This study represents the first example of enantioselective desymmetrization of an inositol under continuous flow conditions. Given the roles of myo ‐inositol derivatives in cell biology research and medicine, practical, sustainable, and efficient preparative procedures for chiral inositols are highly desirable. Upon testing substrate solutions in vinyl acetate/hexanes at various ratios and passing them through a packed‐bed lipase reactor, a home‐made assembly, we identified optimal conditions. Reactions conducted in a 1.0:1.5 vinyl acetate/hexanes mixture at 45 °C achieved conversions of 97–95% with residence times of 2.6–1.6 min, respectively. Notably, reactions in a more hydrophobic solvent system (1.0:2.5 vinyl acetate/hexanes) also showed high conversions (95%) at a 1.6‐min residence time, highlighting the benefits of increased solvent hydrophobicity. Productivity assessments and reuse experiments confirmed the robustness of the biocatalyst under flow conditions, contrasting with a significant decline in performance under batch conditions.
Source: ChemistrySelect
Institution: Universidade Federal do Rio de Janeiro
Language: English
Subfield: Molecular Biology
Domain: Life Sciences
Open Access status: bronze
OpenAlex ID: W4408747695