Synthesis of the Core Oligosaccharides of Lipooligosaccharides from Campylobacter jejuni: A Putative Cause of Guillain-Barré Syndrome.
Chemistry
; 25(3): 796-805, 2019 Jan 14.
Article
em En
| MEDLINE
| ID: mdl-30351481
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.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oligossacarídeos
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Lipopolissacarídeos
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Campylobacter jejuni
Tipo de estudo:
Etiology_studies
Limite:
Humans
Idioma:
En
Revista:
Chemistry
Assunto da revista:
QUIMICA
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Japão