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Glycosyl azide—a novel substrate for enzymatic transglycosylations
Authors:Pavla Fialová  Inmaculada Robina  Petr Sedmera  Lucie Petrásková-Hušáková
Institution:a Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, CZ-142 20 Prague 4, Czech Republic
b Department of Organic Chemistry, Faculty of Chemistry, University of Seville, Aptdo Correros 553, E-41071 Seville, Spain
c Laboratory of High Performance Computing, Institute of Physical Biology USB and Institute of Systems Biology and Ecology AS CR, Zámek 136, CZ-373 33 Nové Hrady, Czech Republic
Abstract:Glycosyl azides are new efficient donors for glycosidases. Their high water solubility facilitates transglycosylations with comparable or better yields than common O-glycosides. The azido group totally changes the β-GalNAc-ase/β-GlcNAc-ase ratio in β-N-acetylhexosaminidases (from the usual 0.3-1.0 to <0.01), contrary to all known aglycons.
Keywords:β-N-Acetylhexosaminidase  Enzyme catalysis  Glycosyl azide  Molecular modelling
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