Catechol glucosides act as donor/acceptor substrates of glucansucrase enzymes of Lactobacillus reuteri

Abstract

Previously, we have shown that the glucansucrase GtfA-ΔN enzyme of Lactobacillus reuteri 121, incubated with sucrose, efficiently glucosylated catechol and we structurally characterized catechol glucosides with up to five glucosyl units attached (te Poele et al. in Bioconjug Chem 27:937–946, 2016). In the present study, we observed that upon prolonged incubation of GtfA-ΔN with 50 mM catechol and 1000 mM sucrose, all catechol had become completely glucosylated and then started to reappear. Following depletion of sucrose, this glucansucrase GtfA-ΔN used both α-d-Glcp-catechol and α-d-Glcp-(1→4)-α-d-Glcp-catechol as donor substrates and transferred a glucose unit to other catechol glycoside molecules or to sugar oligomers. In the absence of sucrose, GtfA-ΔN used α-d-Glcp-catechol both as donor and acceptor substrate to synthesize catechol glucosides with 2 to 10 glucose units attached and formed gluco-oligosaccharides up to a degree of polymerization of 4. Also two other glucansucrases tested, Gtf180-ΔN from L. reuteri 180 and GtfML1-ΔN from L. reuteri ML1, used α-d-Glcp-catechol and di-glucosyl-catechol as donor/acceptor substrate to synthesize both catechol glucosides and gluco-oligosaccharides. With sucrose as donor substrate, the three glucansucrase enzymes also efficiently glucosylated the phenolic compounds pyrogallol, resorcinol, and ethyl gallate; also these mono-glucosides were used as donor/acceptor substrates.Electronic supplementary materialThe online version of this article (doi:10.1007/s00253-017-8190-z) contains supplementary material, which is available to authorized users.

Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

“…The ratio of donor to acceptor suggests that the conversion yield is affected even if a sufficient amount of enzyme is supplied. Similar to the results of this study (Table 1), previous studies reported that the conversion efficiency increased when the concentration of the donor was higher than that of the acceptor [31,39,40]. The enzyme-modified glycosylation of lipophilic compounds is known to be complex because of the low solubility of lipophilic compounds in aqueous systems [41].…”

Polygonatum kingianum Polysaccharides Enhance the Preventive Efficacy of Heat-Inactivated Limosilactobacillus reuteri WX-94 against High-Fat-High-Sucrose-Induced Liver Injury and Gut Dysbacteriosis

“…Specifically, Lactobacilli in general can utilize a great variety of carbohydrates and phytochemicals, thereafter producing various bioactive ingredients with high bioavailability or pharmacological properties, − such as 3-phenyllactic acid, 2-hydroxy-3-(4-hydroxyphenyl)-propanoic acid, lactic acid, propionic acid, arachidic acid, trihydroxyflavone, kojic acid, and succinic acid. − Notably, the contents of these metabolites were significantly higher in the cell-free supernatant of L. reuteri incubated with PKP than in the MRS-cultured L.…”

Characterization of the (Engineered) Branching Sucrase GtfZ-CD2 from Apilactobacillus kunkeei for Efficient Glucosylation of Benzenediol Compounds

“…On one hand, the transglucosylation activity of glucansucrases has been shown to increase with the increase of sucrose concentrations (10). On the other hand, it has been reported that the glucosylated products can be used as donor substrate for glucoside and oligosaccharide synthesis when sucrose is depleted (11), thereby reducing the yield of glucosylated products. In the present study, we found that the glucosylation yields were higher at low acceptor substrate concentrations while high concentrations of acceptors decreased the production of glucosylated products.…”

“…More importantly, for glucosylation reaction, GH70 glucansucrase do not require expensive sugar nucleotides, but use the inexpensive and easily available sucrose as donor substrate (2). Therefore, GH70 family glucansucrases are considered attractive biocatalysts for a-D-glucosylation and have been extensively evaluated for glucosylating various hydroxyl group containing organic molecules, including simple phenolic compounds (such as catechol, resorcinol, and hydroquinone) (9)(10)(11)(12), phenolic acid compounds (such as caffeic acid, ferulic acid, chlorogenic acid, and gallic acid) (13)(14)(15), complex polycyclic flavonoids (16)(17)(18)(19), and linear primary alcohol compounds (9,20,21).…”