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Regioselective galloylation of methyl β-d-glucopyranoside by a lipase

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Abstract

Chromogenic substrate 4-nitrophenyl gallate was prepared in four steps and used for selection of hydrolases specific to gallic ester hydrolysis from among 22 commercial lipases, proteases, and crude glycanase cocktails. Enzymes displaying galloyl esterase activity were tested in regioselective galloylation of methyl β-d-glucopyranoside with vinyl gallate. Lipozyme TL IM in acetonitrile was found to afford the highest conversion (37 %). The reaction proceeded with strict regioselectivity toward the primary hydroxyl of the glucopyranoside ring, giving in preparative scale 27 % of purified methyl 6-O-galloyl-β-d-glucopyranoside as a sole product.

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Acknowledgments

This work was supported by the Slovak Research and Development Agency under the contract No. APVV-0846-12. This publication is also the result of the grant from the Slovak Grant Agency for Science VEGA under the Project No. 2/0138/12 and the Research and Development Operational Programmes funded by the ERDF (“Centre of Excellence on Green Chemistry Methods and Processes”, CEGreenI, Contract No. 26240120001 as well as “Amplification of the Centre of Excellence on Green Chemistry Methods and Processes”, CEGreenII, Contract No. 26240120025).

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Authors and Affiliations

  1. Laboratory of Biocatalysis and Organic Synthesis, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 845 38, Bratislava, Slovakia

    Andrej Chyba, Mária Mastihubová & Vladimír Mastihuba

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  1. Andrej Chyba
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  2. Mária Mastihubová
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  3. Vladimír Mastihuba
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Correspondence to Vladimír Mastihuba.

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Chyba, A., Mastihubová, M. & Mastihuba, V. Regioselective galloylation of methyl β-d-glucopyranoside by a lipase. Monatsh Chem 147, 1137–1142 (2016). https://doi.org/10.1007/s00706-016-1696-8

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  • DOI: https://doi.org/10.1007/s00706-016-1696-8

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