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Biochemical synthesis of novel, self-assembling glycolipids from ricinoleic acid by a recombinant α-glucosidase from Geobacillus sp.

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Abstract

Purpose of work

To explore a novel glycolipid, we performed biochemical reactions using a recombinant α-glucosidase from Geobacillus sp. which shows excellent transglycosylation reaction to hydroxyl groups in a variety of compounds.

Two different glycolipids (GL-1 and GL-2) were prepared from ricinoleic acid using a recombinant α-glucosidase from Geobacillus sp. The molecular structure of GL-1 was confirmed as 12-O-α-d-glucopyranosyl-9-hexadecenoic acid by 1D and 2D NMR analyses. According to MALDI-TOF/MS, GL-1 and GL-2 showed single major peaks at m/z 483.82 and 645.97, respectively. The peaks corresponded to the [M + Na]+ ions of the glycolipids. GL-2 was estimated as 12-O-α-d-glucopyranosyl-(4′-O-α-glucopyranosyl)-9-hexadecenoic acid. Light polarization microscopy revealed that GL-2 easily formed self-assembled vesicles in aqueous solution.

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Acknowledgments

We thanks Dr. Hidehito Takami of the Japan Agency of Marine-Earth Science and Technology (JAMSTEC) for providing Geobacillus sp. HTA-462.

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Correspondence to Masa-aki Konishi.

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Konishi, Ma., Fukuoka, T., Shimane, Y. et al. Biochemical synthesis of novel, self-assembling glycolipids from ricinoleic acid by a recombinant α-glucosidase from Geobacillus sp.. Biotechnol Lett 33, 139–145 (2011). https://doi.org/10.1007/s10529-010-0410-x

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  • DOI: https://doi.org/10.1007/s10529-010-0410-x

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