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Improved synthesis of long-chain alkyl glucosides catalyzed by an engineered β-glucosidase in organic solvents and ionic liquids

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Abstract

Objective

To synthesize octyl β-d-glucopyranoside (OG) and decyl β-d-glucopyranoside (DG) in three non-aqueous reaction systems, namely organic solvents, ionic liquids and co-solvent mixtures, via reverse hydrolysis reactions catalyzed by the N189F dalcochinase mutant.

Results

The highest yield of OG (67 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml−1 enzyme in 20% (v/v) octanol and 70% (v/v) [BMIm][PF6] at 30 °C. On the other hand, the highest yield of DG (64 mol%) was obtained in the reaction containing 0.5 M glucose, 3 unit ml−1 enzyme in 20% (v/v) decanol, 20% (v/v) acetone and 50% (v/v) [BMIm][PF6] at 30 °C. The identities of OG and DG products were confirmed by HRMS and NMR.

Conclusion

This is the first report of enzymatic synthesis of OG and DG via reverse hydrolysis reactions in ionic liquids and co-solvent mixtures. The N189F dalcochinase mutant and the non-aqueous reaction systems described here show great potential for future commercial production of long-chain alkyl glucosides.

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Acknowledgements

This work was financially supported by the Thailand Research Fund and the Commission on Higher Education [RMU5480004]; and the Higher Education Research Promotion and National Research University Project of Thailand. P.T. is a recipient of the Royal Golden Jubilee Ph.D. scholarship from the Thailand Research Fund.

Supporting information

Supplementary Fig. 1—Production of OG (a) and DG (b) via reverse hydrolysis reactions in various percentage ratios of alcochol:organic solvent.

Supplementary Fig. 2—Production of OG (a) and DG (b) via reverse hydrolysis reactions in various percentage ratios of alcohol:acetone.

Supplementary Fig. 3—Production of OG (a) and DG (b) via reverse hydrolysis reactions in various percentage ratios of alcohol:[BMIm][PF6].

Supplementary Fig. 4—Production of OG (a) and DG (b) via reverse hydrolysis reactions in various percentage ratios of alcohol:acetone:[BMIm][PF6].

Supplementary Fig. 5—The 1H-NMR spectra of OG (a) and DG (b), and the 1H-1H COSY spectra of OG (c) and DG (d) using CD3OD as solvent.

Supplementary Table 1—Production of OG and DG via reverse hydrolysis reactions in various percentage ratios of alcohol:[BMIm][PF6].

Supplementary Table 2—Production of OG and DG via reverse hydrolysis reactions in various percentage ratios of alcohol:acetone:[BMIm][PF6 ].

Supplementary Table 3—Mass determination of OG and DG by HRMS

Supplementary Table 4—Synthesis of OG by β-glucosidases via reverse hydrolysis reactions in organic solvent systems.

Supplementary Table 5—Synthesis of alkyl and arylalkyl glycosides by β-glycosidases via reverse hydrolysis reactions in ionic liquids systems.

Author information

Authors and Affiliations

  1. Department of Biochemistry, Faculty of Science, and Center for Advanced Studies in Tropical Natural Resources, NRU-KU, Kasetsart University, Bangkok, Thailand

    Pornpanna Thenchartanan & Prachumporn T. Kongsaeree

  2. Department of Chemistry, Special Research Unit for Advanced Magnetic Resonance and Center of Excellence for Innovation in Chemistry, Faculty of Science, Kasetsart University, Bangkok, Thailand

    Pakorn Wattana-Amorn

  3. Laboratory of Biochemistry, Chulabhorn Research Institute, Bangkok, Thailand

    Jisnuson Svasti

Authors
  1. Pornpanna Thenchartanan
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  2. Pakorn Wattana-Amorn
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  3. Jisnuson Svasti
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  4. Prachumporn T. Kongsaeree
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Correspondence to Prachumporn T. Kongsaeree.

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Thenchartanan, P., Wattana-Amorn, P., Svasti, J. et al. Improved synthesis of long-chain alkyl glucosides catalyzed by an engineered β-glucosidase in organic solvents and ionic liquids. Biotechnol Lett 42, 2379–2387 (2020). https://doi.org/10.1007/s10529-020-02960-8

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  • DOI: https://doi.org/10.1007/s10529-020-02960-8

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