Flow-based biocatalysis: Application to peracetylated arabinofuranosyl-1,5-arabinofuranose synthesis

    • Teodora Bavaroa
    • Andrea Pintob
    • Federica Dall’Oglioc
    • María J. Hernáizd
    • Carlo F. Morellie
    • Paolo Zambellib
    • Carlo De Michelic
    • Paola Contic
    • Lucia Tamborinic
    • Marco Terrenia
    • a Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100 Pavia, Italy
    • b Department of Food Environmental and Nutritional Science (DeFENS), University of Milan, Via Mangiagalli 25, 20133 Milan, Italy
    • c Department of Pharmaceutical Sciences (DISFARM), University of Milan, Via Mangiagalli 25, 20133 Milan, Italy
    • d Department of Pharmaceutical and Organic Chemistry, Faculty of Pharmacy, Complutense University of Madrid, Plaza de Ramón y Cajal s/n, 28040 Madrid, Spain
    • e Department of Chemistry, University of Milan, Via Golgi 19, 20133 Milan, Italy

    The lipase-catalyzed regioselective hydrolysis of peracetylated arabinose was performed in a packed bed flow reactor (PBR). In particular, the hydrolysis of the α  anomer of peracetylated arabinose catalyzed by Novozym® 435 resulted in the monodeprotection of C5 in only 5 min and 91% yield. By using the immobilized Pseudomonas stutzeri lipase, the regioselective hydrolysis of the β  anomer was also accomplished affording the C1 deacetylated derivative in 30 min with good yields. The high local concentration of the immobilized biocatalyst in the PBR allow for a significant reduction of the reaction time; moreover, repeated re-use, and easy downstream processing increase the efficiency and the productivity of the process, if compared to the classical batch procedure. In fact, under optimized conditions, the specific reaction rate of the biocatalyzed flow reaction showed an increase of more than 300 times compared to the batch one. The obtained building blocks were prepared in gram scale and then used for the synthesis of peracetylated arabinofuranosyl-1,5-arabinofuranose.

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