Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharides?

Organic & Biomolecular Chemistry Pub Date: 2012-07-26 DOI: 10.1039/C2OB25855B

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-LewisX (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.

Graphical abstract: Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharides
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