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• W2086331330 endingPage "1877" @default.
• W2086331330 startingPage "1865" @default.
• W2086331330 abstract "C -Glycosylation presents a rare mode of sugar attachment to the core structure of natural products and is catalyzed by a special type of Leloir C -glycosyltransferases (C-GTs). Elucidation of mechanistic principles for these glycosyltransferases (GTs) is of fundamental interest, and it could also contribute to the development of new biocatalysts for the synthesis of valuable C -glycosides, potentially serving as analogues of the highly hydrolysis-sensitive O ‑glycosides. Enzymatic glucosylation of the natural dihydrochalcone phloretin from UDP‑D-glucose was applied as a model reaction in the study of a structurally and functionally homologous pair of plant glucosyltransferases, where the enzyme from rice ( Oryza sativa ) was specific for C -glycosylation and the enzyme from pear ( Pyrus communis ) was specific for O -glycosylation. We show that distinct active-site motifs are used by the two enzymes to differentiate between C - and O -glucosylation of the phloretin acceptor. An enzyme design concept is therefore developed where exchange of active-site motifs results in a reversible switch between C / O -glycosyltransferase (C/O-GT) activity. Mechanistic proposal for enzymatic C -glycosylation involves a single nucleophilic displacement at the glucosyl anomeric carbon, proceeding through an oxocarbenium ion-like transition state. Alternatively, the reaction could be described as Friedel&ndash;Crafts-like direct alkylation of the phenolic acceptor." @default.
• W2086331330 created "2016-06-24" @default.
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• W2086331330 date "2013-07-09" @default.
• W2086331330 modified "2023-09-26" @default.
• W2086331330 title "Enzymatic <i>C</i>-glycosylation: Insights from the study of a complementary pair of plant <i>O</i>- and <i>C</i>-glucosyltransferases" @default.
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• W2086331330 doi "https://doi.org/10.1351/pac-con-12-11-24" @default.
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