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Synthesis, structural characterization, and biological properties of pentyl- and isopentyl-α-D-glucosides

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Abstract

The study was devoted to the synthesis of pentyl glucosides (PenGn) and isopentyl glucosides (Iso-PenGn) by transglycosylation using recombinant cyclodextrin glycosyltransferase from Bacillus circulans A11, β-cyclodextrin as a glucosyl donor and 1-pentanol and isopentanol as acceptors. TLC and MS analysis indicated at least 3 products which were in accordance with PenGn and IsoPenGn having glucose, maltose and maltotriose attached to the alkyl groups of both alcohols. Two products of each glucoside were purified by preparative TLC and their structures were identified by NMR technique to be pentyl-α-D-glucopyranoside (PenG1), pentyl-α-D-maltopyranoside (PenG2), isopentyl-α-D-glucopyranoside (IsoPenG1) and isopentyl- α-D-maltopyranoside (IsoPenG2). The effect of water-in-hexadecane emulsion on emulsion-forming properties showed that PenG2 had the highest emulsifying activity. Adding PenG2 to the insoluble Corynebacterium glutamicum amylomaltase from Escherichia coli transformants (A406R), helped to perform it to more soluble conformation. Moreover, it was found that PenG1,2 exhibited a higher antibacterial activity against E. coli ATCC 25922 than that of IsoPenG1,2. Hence, the biological properties of the synthesized products may be useful for their applications as emulsifying, solubilizing and antibacterial agents.

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References

  1. Takaha, T. and Smith, S.M., Biotechnol. Genet. Eng. Rev., 1999, vol. 16, no. 1, pp. 257–280.

    Article  CAS  PubMed  Google Scholar 

  2. Loftsson, T., Jarho, P., Másson, M., and Järvinen, T., Expert Opin. Drug Deliv., 2005, vol. 2, no. 2, pp. 335–351.

    Article  CAS  PubMed  Google Scholar 

  3. Aramsangtienchai, P., Chavasiri, W., Ito, K., and Pongsawasdi, P., J. Mol. Catal. B: Enzym., 2011, vol. 73, no. 1–4, pp. 27–34.

    Article  CAS  Google Scholar 

  4. Torres, P., Poveda, A., Jimenez–Barbero, J., Parra, J.L., Comelles, F., Ballesteros, A.O., and Plou, F.J., Adv. Synth. Catal., 2011, vol. 353, no. 7, pp. 1077–1086.

    Article  CAS  Google Scholar 

  5. Chotipanang, K., Bhunthumnavin, W., and Prousoontorn, M.H., J. Inclusion Phenom. Macrocyclic Chem., 2011, vol. 70, no. 3, pp. 359–368.

    Article  CAS  Google Scholar 

  6. Wang, Q., Yu, H., Zhao, N., Li, C., Shang, Y., Liu, H., and Xu, J., Chin. J. Catal., 2012, vol. 33, no. 2–3, pp. 275–280.

    Article  Google Scholar 

  7. Lirdprapamongkol, K. and Svasti, J., Biotechnol. Lett., 2000, vol. 22, no. 23, pp. 1889–1894.

    Article  CAS  Google Scholar 

  8. van Rantwijk, F., van Oosterom, M.W., and Sheldon, R.A., J. Mol. Catal. B: Enzym., 1999, vol. 6, no. 6, pp. 511–532.

    Article  Google Scholar 

  9. Bousquet, M.P., Willemot, R.M., Monsan, P., and Boures, E., Appl. Microbiol. Biotechnol., 1998, vol. 50, no. 2, pp. 167–173.

    Article  CAS  Google Scholar 

  10. Itoh, H. and Kamiyama, Y., J. Ferment. Bioeng., 1995, vol. 80, no. 5, pp. 510–512.

    Article  CAS  Google Scholar 

  11. Martearena, M.R., Blanco, S., and Ellenrieder, G., Bioresour. Technol., 2003, vol. 90, no. 3, pp. 297–303.

    Article  CAS  PubMed  Google Scholar 

  12. Kim, Y.M., Kim, B.H., Ahn, J.S., Kim, G.E., Jin, S.D., Nguyen, T.H., and Kim, D., Biotechnol. Lett., 2009, vol. 31, no. 9, pp. 1433–1438.

    Article  CAS  PubMed  Google Scholar 

  13. Istvan, E.S., Hasemann, C.A., Kurumbail, R.G., Uyeda, K., and Deisenhofer, J., Protein Sci., 1995, vol. 4, no. 11, pp. 2439–2441.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Jastrzebska, B., Fotiadis, D., Jang, G.F., Stenkamp, R.E., Engel, A., and Palczewski, K., J. Biol. Chem., 2006, vol. 281, no. 17, pp. 11917–11922.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Kaulpiboon, J., Prasong, W., Rimphanitchayakit, V., Murakami, S., Aoki, K., and Pongsawasdi, P., J. Basic Microbiol., 2010, vol. 50, no. 5, pp. 427–435.

    Article  CAS  PubMed  Google Scholar 

  16. Kato, T. and Horikoshi, K., Biotechnol. Bioeng., 1984, vol. 26, no. 6, pp. 595–598.

    Article  CAS  PubMed  Google Scholar 

  17. Cirigliano, M.C. and Carman, G.M., Appl. Environ. Microbiol., 1984, vol. 48, no. 4, pp. 747–750.

    CAS  PubMed  PubMed Central  Google Scholar 

  18. Nimpiboon, P., Kaulpiboon, J., Krusong, K., Nakamura, S., Kidokoro, S.I., and Pongsawasdi, P., Int. J. Biol. Macromol., 2016, vol. 86, pp. 820–828.

    Article  CAS  PubMed  Google Scholar 

  19. Clinical and Laboratory Standards Institute (CLSI), M100–S24 Performance Standards for Antimicrobial Susceptibility Testing; 24th Informational Supplement, Pennsylvania National Committee for Clinical Laboratory Standards, 2014.

    Google Scholar 

  20. Makropoulou, M., Christakopoulos, P., Tsitsimpikou, C., Kekos, D., Kolisis, F.N., and Macris, B.J., Int. J. Biol. Macromol., 1998, vol. 22, no. 2, pp. 97–101.

    Article  CAS  PubMed  Google Scholar 

  21. Tomasi, R.A., A Spectrum of Spectra, Tulsa Sulbelt R and T Inc., 1997.

    Google Scholar 

  22. Roslund, M.U., Tähtinen, P., Niemitz, M., and Sjöholm, R., Carbohydr. Res., 2008, vol. 343, no. 1, pp. 101–112.

    Article  CAS  PubMed  Google Scholar 

  23. Nakamura, A., Haga, K., and Yamane, K., FEBS Lett., 1994, vol. 337, no. 1, pp. 66–70.

    Article  CAS  PubMed  Google Scholar 

  24. Makowski, K., Bialkowska, A., Olczak, J., Kur, J., and Turkiewicz, M., Enzyme Microb. Technol., 2009, vol. 44, no. 2, pp. 59–64.

    Article  CAS  Google Scholar 

  25. Boyd, B.J., Drummond, C.J., Krodkiewska, I., Weerawardena, A., Furlong, D.N., and Grieser, F., Langmuir, 2001, vol. 17, no. 20, pp. 6100–6107.

    Article  CAS  Google Scholar 

  26. Nainggolan, I., Radiman, S., Hamzah, A.S., and Hashim, R., Colloids Surf., B, 2009, vol. 73, no. 1, pp. 84–91.

    Article  CAS  Google Scholar 

  27. Kleinschmidt, J.H., Wiener, M.C., and Tamm, L.K., Protein Sci., 1999, vol. 8, no. 10, pp. 2065–2071.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. Sánchez–Otero, M.G., Valerio–Alfaro, G., García–Galindo, H.S., and Oliart–Ros, R.M., J. Ind. Microbiol. Biotechnol., 2008, vol. 35, no. 12, pp. 1687–1693.

    Article  PubMed  Google Scholar 

  29. Nimpiboon, P., Krusong, K., Kaulpiboon, J., Kidokoro, S.I., and Pongsawasdi, P., Biochem. Biophys. Res. Commun., 2016, vol. 478, pp. 759–764.

    Article  CAS  PubMed  Google Scholar 

  30. Jones, M.N., Int. J. Pharm., 1999, vol. 177, no. 2, pp. 137–159.

    Article  CAS  PubMed  Google Scholar 

  31. Sułek, M.W., Ogorzałek, M., Wasilewski, T., and Klimaszewska, E., J. Surfactants Deterg., 2013, vol. 16, no. 3, pp. 369–375.

    Article  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Faculty of Medicine, Thammasat University, Pathumthani, 12120, Thailand

    R. Charoensapyanan & J. Kaulpiboon

  2. Department of Agricultural Chemistry, Graduate School of Agriculture, Meiji University, Tamaku, Kawasaki, 214-8571, Japan

    Y. Takahashi & S. Murakami

  3. Department of Biology, Graduate School of Science, Osaka City University, Osaka, 558-8585, Japan

    K. Ito

  4. Department of Biochemistry, Phramongkutklao College of Medicine, Bangkok, 10400, Thailand

    P. Rudeekulthamrong

Authors
  1. R. Charoensapyanan
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  2. Y. Takahashi
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  3. S. Murakami
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  4. K. Ito
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  5. P. Rudeekulthamrong
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  6. J. Kaulpiboon
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Correspondence to P. Rudeekulthamrong.

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Charoensapyanan, R., Takahashi, Y., Murakami, S. et al. Synthesis, structural characterization, and biological properties of pentyl- and isopentyl-α-D-glucosides. Appl Biochem Microbiol 53, 410–420 (2017). https://doi.org/10.1134/S0003683817040020

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  • DOI: https://doi.org/10.1134/S0003683817040020

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