Abstract
Objective
To determine the transglycosylation activity of cell-bound enzymes from Microbacterium paraoxydans to catalyze the synthesis of hexyl-α-d-glucoside (HG) and -polyglucosides using sucrose as a glycosyl donor.
Results
Maximum HG yield (14.8 %) was achieved at 0.96 water activity in 12 h with sucrose at 0.5 M with lyophilized cells (equivalent to 8 IU α-glucosidase activity). The synthesized alkyl-glucosides and-polyglucosides were characterized by ESI-MS. Structural elucidation of the main product (purified by solid phase chromatography) was done by HSQC (2D NMR) which was confirmed as 1-hexyl-α-d-glucopyranoside. The synthesis was scaled up in a fed-batch reactor, with continuous feeding of whole cells every 6 h and a total yield of ~44 % was obtained for hexyl-glucoside and -polyglucosides under the optimized conditions.
Conclusion
Synthesis of HG, hexyl di- and tri-glucosides has been achieved using a novel method.
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Acknowledgments
This study was supported by Defense Research and Development Organization, India. Thanks are extended to Advance Instrumentation Research Facility, JNU, for NMR analysis.
Supporting information
Supplementary Fig. 1—TLC plate showing the formation of hexyl mono-, di- and tri- glucosides. Lanes 1-5: Standard HG (15,20,30,40 and 50 μg respectively), Lanes 8-12: Standard hexyl –diglucoside (15,20,30,40 and 50 μg respectively), Lanes 15-19: Standard hexyl-triglucoside (15,20,30,40 and 50 μg respectively), Lanes 6-7, 13-14, 20-21: Synthesized products after 24 h incubation.
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Dahiya, S., Ojha, S. & Mishra, S. Biotransformation of sucrose into hexyl-α-d-glucopyranoside and -polyglucosides by whole cells of Microbacterium paraoxydans . Biotechnol Lett 37, 1431–1437 (2015). https://doi.org/10.1007/s10529-015-1808-2
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DOI: https://doi.org/10.1007/s10529-015-1808-2