Extending the Scope of GTFR Glucosylation Reactions with Tosylated Substrates for Rare Sugars Synthesis |
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Authors: | Julian Görl Christian Possiel Prof. Dr. Christoph Sotriffer Prof. Dr. Jürgen Seibel |
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Affiliation: | 1. Department of Organic Chemistry, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany;2. Department of Pharmacy and Food Chemistry, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany |
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Abstract: | Functionalized rare sugars were synthesized with 2-, 3-, and 6-tosylated glucose derivatives as acceptor substrates by transglucosylation with sucrose and the glucansucrase GTFR from Streptococcus oralis. The 2- and 3-tosylated glucose derivatives yielded the corresponding 1,6-linked disaccharides (isomaltose analogues), whereas the 6-tosylated glucose derivatives resulted in 1,3-linked disaccharides (nigerose analogue) with high regioselectivity in up to 95 % yield. Docking studies provided insight into the binding mode of the acceptors and suggested two different orientations that were responsible for the change in regioselectivity. |
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Keywords: | biocatalysis carbohydrates glucansucrase substrate engineering substrate promiscuity |
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