title: Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharides.
abstract: 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 (GlcNAc) 1, I-Tag2-LacNAc (Galβ(1-4)GlcNAc) 2 and I-Tag2-Lewis(X) (Galβ(1-4)[Fucα(1-3)]GlcNAc) 3, which are oligosaccharides of biological relevance, were enzymatically prepared. The apparent kinetic parameters for the enzyme catalysed transformations with β-1,4-galactosyltransferase (β-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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK. M.C.Galan@bristol.ac.uk
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Galan
authors.forename: Anh Tuan
authors.initials: AT
authors.lastname: Tran
authors.forename: Karen
authors.initials: K
authors.lastname: Bromfield
authors.forename: Said
authors.initials: S
authors.lastname: Rabbani
authors.forename: Beat
authors.initials: B
authors.lastname: Ernst
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D016466:CHO Cells; D002240:Carbohydrate Sequence; D006224:Cricetinae; D005647:Fucosyltransferases / Q000378:metabolism; D005700:Galactosyltransferases / Q000378:metabolism; D006031:Glycosylation; D052578:Ionic Liquids / Q000737:chemistry*; D007700:Kinetics; D013058:Mass Spectrometry / Q000379:methods; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D052578:Ionic Liquids; D009844:Oligosaccharides; D005647:Fucosyltransferases; D005700:Galactosyltransferases; D000117:Acetylglucosamine