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- W2897867508 abstract "The chemical synthesis of the highly branched core oligosaccharides of lipooligosaccharides (LOSs) found in Campylobacter jejuni, which causes Guillain-Barré syndrome by a preceding infection, is described. The target LOS mimics, consisting of eight or nine monosaccharides, were classified into three groups as key building blocks: ganglioside-core tetra-/pentasaccharides (GM1-/GD1a-like), l-glycero-d-manno-heptose-containing trisaccharides, and 3-deoxy-d-manno-2-octulosonic acid (KDO) residues. These synthetic fragments were obtained from commercially available monosaccharides. Less obtainable l-glycero-d-manno-heptose and KDO residues, as key components of the LOSs, were synthesized from p-methoxyphenyl d-mannoside and di-O-isopropylidene-protected d-mannose, respectively. The synthesis of α-KDO glycoside, as one of the most difficult stereocontrolled glycosidic constructions, was achieved by treating a 2,3-ene derivative of KDO with phenylselenyl trifluoromethanesulfonate as a suitable α-directing reagent. All synthetic blocks were constructed through a convergent synthetic route, which resulted in the first synthesis of structurally challenging LOS core glycans containing ganglioside GM1 and GD1a-core sequences." @default.
- W2897867508 created "2018-10-26" @default.
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- W2897867508 date "2018-12-13" @default.
- W2897867508 modified "2023-10-17" @default.
- W2897867508 title "Synthesis of the Core Oligosaccharides of Lipooligosaccharides from <i>Campylobacter jejuni</i> : A Putative Cause of Guillain–Barré Syndrome" @default.
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- W2897867508 doi "https://doi.org/10.1002/chem.201804862" @default.
- W2897867508 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/30351481" @default.
- W2897867508 hasPublicationYear "2018" @default.
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