Regioselective glucosylation of inositols catalyzed by Thermoanaerobacter sp. CGTase

[Display omitted] ► CGTase from Thermoanaerobacter sp. transfers glucose residues to four inositols. ► With the exception of d-pinitol, all inositols were able to act as acceptors. ► The configuration of d-glucose at 2, 3, and 4 define the specificity. Monoglucosylated products of l-chiro-, d-chiro-...

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Bibliographic Details
Published in:Carbohydrate research 2012-10, Vol.360, p.93-101
Main Authors: Miranda-Molina, Alfonso, Marquina-Bahena, Silvia, López-Munguía, Agustín, Álvarez, Laura, Castillo, Edmundo
Format: Article
Language:English
Subjects:
Biocatalysis
Carbohydrate Conformation
CGTase
Configuration
Glucoamylase
Glucosyltransferases - metabolism
Glycosylation
Inositol - biosynthesis
Inositol - chemistry
Inositols
Regiopecificity
Stereoisomerism
Thermoanaerobacter - enzymology
α-d-Glucosylation
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Summary:[Display omitted] ► CGTase from Thermoanaerobacter sp. transfers glucose residues to four inositols. ► With the exception of d-pinitol, all inositols were able to act as acceptors. ► The configuration of d-glucose at 2, 3, and 4 define the specificity. Monoglucosylated products of l-chiro-, d-chiro-, muco-, and allo-inositol were synthesized by regioselective α-d-glucosylation with cyclodextrin glucosyl transferase from Thermoanaerobacter sp. after hydrolysis of by products with Aspergillus niger glucoamylase. While the reactions carried out with d-chiro-, muco-, and allo-inositol resulted in the regioselective formation of monoglucosylated products, two products were obtained in the reaction with l-chiro-inositol. Through the structural characterization of the glucosylated inositols here we demonstrated that the selectivity observed in the glucosylation of several inositols by Thermoanaerobacter sp. CGTase, is analogous to the specificity observed for the glucosylation of β-d-glucopyranose and equivalent glucosides.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2012.08.002