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

Carbohydr Res

Department of Surgery, Center for Drug Discovery and Translational Research, Beth Israel Deaconess Medical Center, Harvard Medical School, 110 Francis Street, Suite 9F, Boston, MA 02215, USA; Wyss Institute of Biologically Inspired Engineering, Harvard University, 110 Francis Street, Suite 9F, Boston, MA 02115, USA; Harvard-MIT Division of Health Sciences and Technology, Cambridge, MA 02139, USA. Electronic address:

Published: November 2017

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).

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5682196PMC
http://dx.doi.org/10.1016/j.carres.2017.10.002DOI Listing

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