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Miguez N.,CSIC - Institute of Catalysis | Poveda A.,bio Center for Cooperative Research in Biosciences | Plou F.J.,CSIC - Institute of Catalysis
Applied Microbiology and Biotechnology | Year: 2016

The β-fructofuranosidase from the yeast Schwanniomyces occidentalis (Ffase) produces the prebiotic sugars 6-kestose and 1-kestose by transfructosylation of sucrose, which makes it of biotechnological interest. In this study, the hydrolase and transferase activity of this enzyme was kinetically characterized and its potential to synthesize new fructosylated products explored. A total of 40 hydroxylated compounds were used as potential fructosyl-acceptor alternatives to sucrose. Only 17 of them, including some monosaccharides, disaccharides, and oligosaccharides as well as alditols and glycosides were fructosylated. The best alternative acceptors were the alditols. The major transfer product of the reaction including mannitol was purified and characterized as 1-O-β-d-fructofuranosyl-d-mannitol, whose maximum concentration reached 44 g/L, representing about 7.3 % of total compounds in the mixture and 89 % of all products generated by transfructosylation. The reactions including erythritol produced 35 g/L of an isomer mixture comprising 1- and 4-O-β-d-fructofuranosyl-d-erythritol. In addition, Ffase produced 24 g/L of the disaccharide blastose by direct fructosylation of glucose, which makes it the first enzyme characterized from yeast showing this ability. Thus, novel fructosylated compounds with potential applications in food and pharmaceutical industries can be obtained due to the Ffase fructosyl-acceptor promiscuity. © 2016 Springer-Verlag Berlin Heidelberg

Fernandez-Tejada A.,CSIC - Biological Research Center | Canada F.J.,CSIC - Biological Research Center | Jimenez-Barbero J.,bio Center for Cooperative Research in Biosciences | Jimenez-Barbero J.,Ikerbasque
ChemMedChem | Year: 2015

The biological relevance of glycans as mediators of key physiological processes, including disease-related mechanisms, makes them attractive targets for a wide range of medical applications. Despite their important biological roles, especially as molecular recognition elements, carbohydrates have not been fully exploited as therapeutics mainly due to the scarcity of structure-activity correlations and their non-drug-like properties. A more detailed understanding of the complex carbohydrate structures and their associated functions should contribute to the development of new glycan-based pharmaceuticals. Recent significant progress in oligosaccharide synthesis and chemical glycobiology has renewed the interest of the medicinal chemistry community in carbohydrates. This promises to increase our possibilities to harness them in drug discovery efforts for the development of new and more effective, synthetic glycan-based therapeutics and vaccines. Keeping drug discovery sweet! Glycans are an important, though underexploited, platform in medicinal chemistry. Here, relevant examples are used to highlight the potential of oligosaccharides in chemistry, biology, and medicine. Key research and development trends in glycoscience, including carbohydrate-derived drugs, vaccines and therapeutic glycoproteins, are summarized with a view towards future, promising directions in the field for drug discovery purposes and biomedical applications. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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