Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharidesElectronic supplementary information (ESI) available: NMR traces for all novel compounds. See DOI: 10.1039/c2ob25855b

• Main Authors: Galan, M. Carmen, Tran, Anh Tuan, Bromfield, Karen, Rabbani, Said, Ernst, Beat
• Format: Article
• Language: English
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/c2ob25855b

A new N -benzenesulfonyl-based ionic-liquid mass spectroscopy label (I-Tag2) for covalent attachment to substrates has been prepared. I-Tag2 was used to monitor oligosaccharide elongation and serve as a purification handle. Starting from chemically synthesized I-Tag2-labelled N -acetyl glucosamine (Glc N Ac) 1 , I-Tag2-Lac N Ac (Gal(1-4)Glc N Ac) 2 and I-Tag2-Lewis X (Gal(1-4)[Fuc(1-3)]Glc N Ac) 3 , which are oligosaccharides of biological relevance, were enzymatically prepared. The apparent kinetic parameters for the enzyme catalysed transformations with -1,4-galactosyltransferase (-1,4-GalT) and fucosyltransferase VI (FucT VI) were measured by LC-MS demonstrating the applicability and versatility of the new I-Tags in enzymatic transformations with glycosyltransferases. A new N -benzenesulfonyl-based ionic liquid mass spectroscopy label (I-Tag2) for covalent attachment to glycan substrates has been prepared that can be used to monitor oligosaccharide elongation and serve as a purification handle.