Investigating the Potential of Phenolic Compounds and Carbohydrates as Acceptor Substrates for Levansucrase‐Catalyzed Transfructosylation Reaction

• Published in: Chembiochem : a European journal of chemical biology 2024-05, Vol.25 (10), p.e202400107-n/a
• Main Authors: Wong Min, Muriel, Liu, Lan, Karboune, Salwa
• Format: Article
• Language: English
• Subjects: Acceptor specificity; Biocatalysis; Carbohydrates; Chemical reactions; Epicatechin; Fructooligosaccharides; Fructosylated trisaccharides; Glycosylation; Hydroxyl groups; Levansucrase; Maltose; Phenolic compounds; Phenolic fructosides; Phenols; Substrates; Sucrose
• ISSN: 1439-4227; 1439-7633
• DOI: 10.1002/cbic.202400107

This study characterizes the acceptor specificity of levansucrases (LSs) from Gluconobacter oxydans (LS1), Vibrio natriegens (LS2), Novosphingobium aromaticivorans (LS3), and Paraburkholderia graminis (LS4) using sucrose as fructosyl donor and selected phenolic compounds and carbohydrates as acceptors. Overall, V. natriegens LS2 proved to be the best biocatalyst for the transfructosylation of phenolic compounds. More than one fructosyl unit could be attached to fructosylated phenolic compounds. The transfructosylation of epicatechin by P. graminis LS4 resulted in the most diversified products, with up to five fructosyl units transferred. In addition to the LS source, the acceptor specificity of LS towards phenolic compounds and their transfructosylation products were found to greatly depend on their chemical structure: the number of phenolic rings, the reactivity of hydroxyl groups and the presence of aliphatic chains or methoxy groups. Similarly, for carbohydrates, the transfructosylation yield was dependent on both the LS source and the acceptor type. The highest yield of fructosylated‐trisaccharides was Erlose from the transfructosylation of maltose catalyzed by LS2, with production reaching 200 g/L. LS2 was more selective towards the transfructosylation of phenolic compounds and carbohydrates, while reactions catalyzed by LS1, LS3 and LS4 also produced fructooligosaccharides. This study shows the high potential for the application of LSs in the glycosylation of phenolic compounds and carbohydrates. Levansucrases from Gluconobacter oxydans, Vibrio natriegens, Novosphingobium aromaticivorans, and Paraburkholderia graminis were used to catalyze the transfructosylation of phenolic compounds and carbohydrates. The selected phenolic acceptor substrates were successfully glycosylated with up to five fructosyl groups transferred from the sucrose donor substrate. The transfructosylation of carbohydrates acceptors produced fructosylated trisaccharides that can act as low‐calorie sugar substitutes and/or prebiotic ingredients.