Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes

Bioorganic & Medicinal Chemistry Letters
Imke Sittel, M Carmen Galan

Abstract

Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.

References

Sep 1, 2001·Biochimie·A Harduin-LepersP Delannoy
May 3, 2008·Carbohydrate Research·Cristina De Meo, Uvege Priyadarshani
Jul 9, 2008·Trends in Molecular Medicine·Ajit Varki
Dec 22, 2009·ACS Chemical Biology·Xi Chen, Ajit Varki

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Citations

Mar 15, 2016·Chemical Communications : Chem Comm·David Benito-AlifonsoM Carmen Galan
Jun 6, 2019·Organic & Biomolecular Chemistry·Kun HuangSabine L Flitsch
Apr 20, 2021·Journal of the American Society for Mass Spectrometry·Beatriz CalleStacy A Malaker
Jun 22, 2021·Journal of Agricultural and Food Chemistry·M Karimi AlavijehS E Kentish
Jun 24, 2021·Chemical Communications : Chem Comm·Yao-Yao ZhangM Carmen Galan

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