Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides

Citation:

Sardar MYR, Krishnamurthy VR, Park S, Mandhapati AR, Wever WJ, Park D, Cummings RD, Chaikof EL. Synthesis of LewisX-O-Core-1 threonine: A building block for O-linked LewisX glycopeptides. Carbohydrate Research. 2017;452 (17) :47-53.

Abstract:

LewisX (LeX) 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 LeX remains a major limitation for structure-function studies of the LeX determinant. Here we report a total synthesis of a LeX 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 LeX glycopeptides. The described approach is broadly applicable to the synthesis of a variety of complex glycopeptides containing O-linked LeX or sialyl LewisX (sLeX).

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