| Literature DB >> 29065342 |
Mohammed Y R Sardar1, Venkata R Krishnamurthy1, Simon Park1, Appi Reddy Mandhapati1, Walter J Wever1, Dayoung Park1, Richard D Cummings2, Elliot L Chaikof3.
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).Entities:
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Year: 2017 PMID： 29065342 PMCID： PMC5682196 DOI： 10.1016/j.carres.2017.10.002
Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104