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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Non-isosteric C-glycosyl analogues of natural nucleotide diphosphate sugars as glycosyltransferase inhibitors.

A series of C-glycosyl ethylphosphonophosphate analogues of UDP-Glc, UDP-Gal, UDP-GlcNAc and GDP-Fuc were synthesized from the corresponding C-glycosyl ethylphosphonic acids. Analogues were obtained as alpha-anomers through either diastereoselective photo-induced radical addition of glycosyl bromides (d-Glc, d-Gal and l-Fuc) to diethyl vinylphosphonate, or a multi-step sequence (d-GlcNAc), with subsequent coupling with morpholidate-activated nucleotide monophosphates. The in vitro inhibitory activity of UDP-Gal, GDP-Fuc and UDP-GlcNAc analogues towards glycosyltransferases (beta-1,4-GalT, FUT3 and LgtA) was evaluated through a competition fluorescence assay and IC(50) values of 40muM, 2mM and 3.5mM were obtained, respectively.[1]

References

  1. Non-isosteric C-glycosyl analogues of natural nucleotide diphosphate sugars as glycosyltransferase inhibitors. Vidal, S., Bruyère, I., Malleron, A., Augé, C., Praly, J.P. Bioorg. Med. Chem. (2006) [Pubmed]
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