Glucosylation of Catechol with the GTFA Glucansucrase Enzyme from Lactobacillus reuteri and Sucrose as Donor Substrate

Bioconjugate Chemistry
Evelien M te PoeleLubbert Dijkhuizen

Abstract

Lactic acid bacteria use glucansucrase enzymes for synthesis of gluco-oligosaccharides and polysaccharides (α-glucans) from sucrose. Depending on the glucansucrase enzyme, specific α-glucosidic linkages are introduced. GTFA-ΔN (N-terminally truncated glucosyltransferase A) is a glucansucrase enzyme of Lactobacillus reuteri 121 that synthesizes the reuteran polysaccharide with (α1 → 4) and (α1 → 6) glycosidic linkages. Glucansucrases also catalyze glucosylation of various alternative acceptor substrates. At present it is unclear whether the linkage specificity of these enzymes is the same in oligo/polysaccharide synthesis and in glucosylation of alternative acceptor substrates. Our results show that GTFA-ΔN glucosylates catechol into products with up to at least 5 glucosyl units attached. These catechol glucosides were isolated and structurally characterized using 1D/2D (1)H NMR spectroscopy. They contained 1 to 5 glucose units with different (α1 → 4) and (α1 → 6) glycosidic linkage combinations. Interestingly, a branched catechol glucoside was also formed along with a catechol glucoside with 2 successive (α1 → 6) glycosidic linkages, products that are absent when only sucrose is used as both glycosyl donor and acceptor substrate.

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Citations

Mar 5, 2017·Applied Microbiology and Biotechnology·Evelien M Te PoeleLubbert Dijkhuizen
Apr 21, 2017·Chembiochem : a European Journal of Chemical Biology·Rama Krishna Gudiminchi, Bernd Nidetzky
Nov 19, 2019·Journal of Agricultural and Food Chemistry·Tizian KlingelDaniel Wefers
Oct 11, 2020·International Journal of Biological Macromolecules·Dawei NiWanmeng Mu
Dec 16, 2021·Critical Reviews in Food Science and Nutrition·Xiaodan LiWeifeng Liu

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