Synthesis of Lewis X - O -Core-1 threonine: A building block for O -linked Lewis X glycopeptides
| Autor: | Richard D. Cummings, Walter Wever, Appi Reddy Mandhapati, Dayoung Park, Mohammed Y. R. Sardar, Simon S. Park, Elliot L. Chaikof, Venkata R. Krishnamurthy |
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| Rok vydání: | 2017 |
| Předmět: |
0301 basic medicine
chemistry.chemical_classification Glycosylation Stereochemistry Organic Chemistry Total synthesis General Medicine Biochemistry Combinatorial chemistry Glycopeptide Analytical Chemistry Amino acid 03 medical and health sciences chemistry.chemical_compound 030104 developmental biology chemistry Solid-Phase Synthesis Techniques Peptide synthesis Trisaccharide Threonine |
| Zdroj: | Carbohydrate Research. 452:47-53 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2017.10.002 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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