Abstract
Imidazolium-labeled (ITag-) glycosides are used to harness the glycosyltransferase activity directly from human breast milk. The covalently attached ionic labels provide a bifunctional chemical handle that is used to monitor reaction progress by MS, as well as aid in product purification from complex mixtures. The technology is exemplified in the synthesis of biologically relevant oligosaccharide analogs, LacNAc-ITag, ITag-Lewisx and ITag-Lewisa, in a matter of days from human breast milk without having to isolate specific enzymes.
Highlights
Imidazolium-labeled (ITag-) glycosides are used to harness the glycosyltransferase activity directly from human breast milk
The technology is exemplified in the synthesis of biologically relevant oligosaccharide analogs, LacNAc-imidazolium-based tags (ITags), ITag-Lewisx and ITag-Lewisa, in a matter of days from human breast milk without having to isolate specific enzymes
In our work, we demonstrated that the cationic labels are compatible with enzymatic transformations and that ITagglycoside substrates could be employed for the qualitative and quantitative reaction monitoring, using mass spectrometry (MS) techniques, of bovine milk β-1,4-galactosyltransferase (β-1,4-GalT),[13] human α-1,3-fucosyltransferase (α-1,3-FucT VI)[14] and α-2,3-sialyltransferase (α-2,3-ST) from pasteurella multocida, as well as α-2,6-sialyltransferase (α-2,6-ST)[15] from photobacterium damsela
Summary
Imidazolium-labeled (ITag-) glycosides are used to harness the glycosyltransferase activity directly from human breast milk.
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