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Issue 35, 2012
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Ionic-liquid-based MS probes for the chemo-enzymatic synthesis of oligosaccharides

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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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Supplementary files

Article information


Submitted
04 May 2012
Accepted
25 Jul 2012
First published
26 Jul 2012

Org. Biomol. Chem., 2012,10, 7091-7097
Article type
Paper

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

M. C. Galan, A. T. Tran, K. Bromfield, S. Rabbani and B. Ernst, Org. Biomol. Chem., 2012, 10, 7091
DOI: 10.1039/C2OB25855B

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