Biocatalytic production of novel glycolipids with cellodextrin phosphorylase

• Published in: Bioresource technology Vol. 115; pp. 84 - 87
• Main Authors: Tran, Hai Giang, Desmet, Tom, Saerens, Karen, Waegeman, Hendrik, Vandekerckhove, Stéphanie, D’hooghe, Matthias, Van Bogaert, Inge, Soetaert, Wim
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.07.2012
• Subjects: Biocatalysis; Biosurfactant; biosurfactants; Cellodextrin phosphorylase; Clostridium; Clostridium - enzymology; Clostridium stercorarium; Enzymes; Fermentation; Glucosyltransferases - metabolism; Glycolipid; glycolipids; Glycolipids - biosynthesis; Glycosylation; Hydrogen-Ion Concentration; industry; Kinetics; Nanomaterials; phosphorylase; Phosphorylases; Substrate Specificity; Surfactants; Synthesis; Temperature; Thermodynamic equilibrium; Biosurfactant; Glycosylation; Biocatalysis; Cellodextrin phosphorylase; Glycolipid
• ISSN: 0960-8524; 1873-2976
• DOI: 10.1016/j.biortech.2011.09.085

► Cellodextrin phosphorylase from Clostridium stercorarium is able to synthesize new glycolipids. ► Glucolipid and sophorolipid acceptors are extended with one or two glucosyl moieties. ► Product precipitation drives the reactions to near completion and facilitates purification. ► The glycosyl donor α-galactose 1-phosphate allows the synthesis of lactolipid in highly pure form. Glycolipids have gained increasing attention as natural surfactants with a beneficial environmental profile. They are typically produced by fermentation, which only gives access to a limited number of structures. Here we describe the biocatalytic production of novel glycolipids with the cellodextrin phosphorylase from Clostridium stercorarium. This enzyme was found to display a broad donor and acceptor specificity, allowing the synthesis of five different products. Indeed, using either α-glucose 1-phosphate or α-galactose 1-phosphate as glycosyl donor, sophorolipid as well as glucolipid could be efficiently glycosylated. The transfer of a glucosyl moiety afforded a mixture of products that precipitated from the solution, resulting in near quantitative yields. The transfer of a galactosyl moiety, in contrast, generated a single product that remained in solution at thermodynamic equilibrium. These glycolipids not only serve as a new class of biosurfactants, but could also have applications in the pharmaceutical and nanomaterials industries.