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


ABSTRACT: LewisX (LeX) is a branched trisaccharide Gal?1?4(Fuc?1?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).

SUBMITTER: Sardar MYR 

PROVIDER: S-EPMC5682196 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Synthesis of Lewis<sup>X</sup>-O-Core-1 threonine: A building block for O-linked Lewis<sup>X</sup> glycopeptides.

Sardar Mohammed Y R MYR   Krishnamurthy Venkata R VR   Park Simon S   Mandhapati Appi Reddy AR   Wever Walter J WJ   Park Dayoung D   Cummings Richard D RD   Chaikof Elliot L EL  

Carbohydrate research 20171010


Lewis<sup>X</sup> (Le<sup>X</sup>) 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<sup>X</sup> remains a major limitation for structure-function studies of the Le<sup>X</sup> determinant. Here we report a total synthesis of a Le<sup>X</sup> pentasaccharide 1 using a regioselective 1-benzenesulfinyl piperidine/triflic an  ...[more]

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