title: 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.
authors.affiliation: Microbial Physiology Research Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands.
authors.forename: Evelien M
authors.initials: EM
authors.lastname: Te Poele
authors.affiliation: Microbial Physiology Research Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands.
authors.forename: Vincent
authors.initials: V
authors.lastname: Valk
authors.affiliation: Microbial Physiology Research Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands.|Centre for Industrial Biotechnology and Biocatalysis, Department of Biochemical and Microbial Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000, Ghent, Belgium.
authors.forename: Tim
authors.initials: T
authors.lastname: Devlamynck
authors.affiliation: Microbial Physiology Research Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands.
authors.forename: Sander S
authors.initials: SS
authors.lastname: van Leeuwen
authors.affiliation: Microbial Physiology Research Group, Groningen Biomolecular Sciences and Biotechnology Institute (GBB), University of Groningen, Groningen, The Netherlands. l.dijkhuizen@rug.nl.
authors.forename: Lubbert
authors.initials: L
authors.lastname: Dijkhuizen
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism; D002396:Catechols / Q000378:metabolism* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D005960:Glucosides / Q000378:metabolism*; D006031:Glycosylation; D016695:Glycosyltransferases / Q000096:biosynthesis / Q000378:metabolism*; D052200:Limosilactobacillus reuteri / Q000187:drug effects / Q000201:enzymology*; D009844:Oligosaccharides / Q000737:chemistry; D011748:Pyrogallol / Q000378:metabolism; D012118:Resorcinols / Q000378:metabolism; D013395:Sucrose / Q000494:pharmacology
chemical_list: D001426:Bacterial Proteins; D002396:Catechols; D005960:Glucosides; D009844:Oligosaccharides; D012118:Resorcinols; D011748:Pyrogallol; C048734:ethyl gallate; D013395:Sucrose; D005707:Gallic Acid; D016695:Glycosyltransferases; C033837:alternansucrase; D005947:Glucose; C034221:catechol; C031389:resorcinol
keywords: Acceptor reaction; Catechol glucosides; Glucansucrase; Glucosyl donor; Lactobacillus reuteri