Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
NCBI PubMed ID: 30351481Publication DOI: 10.1002/chem.201804862Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: Akihiro Imamura <aimamura
gifu-u.ac.jp>; Hideharu Ishida <ishida
cc.gifu-u.ac.jp>
Institutions: Department of Applied Bio-organic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu, 501-1193, Japan, Center for Highly Advanced Integration and Nano and Life Sciences, (G-CHAIN), Gifu University, 1-1 Yanagido, Gifu-shi, Gifu, 501-1193, Japan, Structural Glycobiology Team, Systems Glycobiology Research Group, RIKEN Global Research Cluster, 2-1 Hirosawa, Wako, Saitama, 351-0198, Japan
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 alpha-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.
chemistry, structural, group, Research, gangliosides, Guillain-Barre syndrome, cluster, lipooligosaccharides, glycosylation, PDF, Science, glycobiology, arbohydrates
Structure type: oligomer
Location inside paper: p.797, fig.1(a)
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_134627,IEDB_136044,IEDB_136794,IEDB_137472,IEDB_137473,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146100,IEDB_146664,IEDB_147450,IEDB_147451,IEDB_149174,IEDB_150933,IEDB_190606,IEDB_2189047,IEDB_983931,SB_116,SB_165,SB_166,SB_170,SB_171,SB_172,SB_187,SB_192,SB_195,SB_23,SB_24,SB_25,SB_39,SB_68,SB_7,SB_8,SB_84,SB_88,SB_96
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, UV, glycosylation, optical rotation measurement, ESI-TOF-MS, flash chromatography
Comments, role: lipooligosaccharide, mimic of human ganglioside GM1
Related record ID(s): 2360
NCBI Taxonomy refs (TaxIDs): 197Reference(s) to other database(s): GTC:G99874JB
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There is only one chemically distinct structure:
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