Chemoselective Elaboration of O-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAc
- 1 February 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (8), 1587-1595
- https://doi.org/10.1021/ja003713q
Abstract
A critical branch point in mucin-type oligosaccharides is the β1 → 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was incorporated into a peptide by fluorenylmethoxycarbonyl (Fmoc)-based solid-phase peptide synthesis. Higher order oligosaccharides were readily generated by alkylation of the corresponding 3-thioGalNAc with N-bromoacetamido sugars. The rapid assembly of “core 1”and “core 3” O-linked glycopeptide mimetics was accomplished in this fashion.Keywords
This publication has 62 references indexed in Scilit:
- Noncovalent Association of P-selectin Glycoprotein Ligand-1 and Minimal Determinants for Binding to P-selectinJournal of Biological Chemistry, 2000
- A Broadly Applicable Method for the Efficient Synthesis of α-O-Linked Glycopeptides and Clustered Sialic Acid ResiduesJournal of the American Chemical Society, 1999
- Synthesis of glycopeptide sequences of repeating units of the mucins MUC 2 and MUC 3 containing oligosaccharide side-chains with core 1, core 2, core 3, core 4 and core 6 structureJournal of the Chemical Society, Perkin Transactions 1, 1997
- Non-Carbohydrate Route to Levoglucosenone and Its Enantiomer Employing Asymmetric DihydroxylationSynlett, 1996
- Synthese von O‐Glycopeptid‐Sequenzen des N‐Terminus von Interleukin‐2European Journal of Organic Chemistry, 1989
- Bausteine von Oligosacchariden, XI: Synthese α‐glycosidisch verknüpfter Disaccharide der 2‐Amino‐2‐desoxy‐D‐galactopyranoseEuropean Journal of Inorganic Chemistry, 1978
- The Structure and Methods of Synthesis of ThiiransRussian Chemical Reviews, 1975
- The Reaction of Epoxides with Thiourea1Journal of the American Chemical Society, 1953
- The Formation and Ring-Opening of Alkene SulfidesJournal of the American Chemical Society, 1951
- Synthesis of the Natural Antithyroid Factor l-5-Vinyl-2-thioöxazolidone1Journal of the American Chemical Society, 1950