Lewis (Le) is a branched trisaccharide Galβ1→4(Fucα1→3)GlcNAc that is expressed on many cell surface glycoproteins and plays critical roles in innate and adaptive immune responses. However, efficient synthesis of glycopeptides bearing Le remains a major limitation for structure-function studies of the Le determinant. Here we report a total synthesis of a Le pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic anhydride promoted [3 + 2] glycosylation. The presence of an Fmoc-threonine amino acid facilitates incorporation of the pentasaccharide in solid phase peptide synthesis, providing a route to diverse O-linked Le glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked Le or sialyl Lewis (sLe).
Download full-text PDF |
Source |
---|---|
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5682196 | PMC |
http://dx.doi.org/10.1016/j.carres.2017.10.002 | DOI Listing |
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!