Synthesis of the Core Oligosaccharides of Lipooligosaccharides from Campylobacter jejuni: A Putative Cause of Guillain-Barré Syndrome.

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.

• Authors: Fumi Yoshida, Hiroki Yoshinaka, Hidenori Tanaka, Shinya Hanashima, Yoshiki Yamaguchi, Mikio Ishihara, Miyuki Saburomaru, Yuki Kato, Risa Saito, Hiromune Ando, Makoto Kiso, Akihiro Imamura, Hideharu Ishida
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 25 Issue 3 Pg. 796-805 (Jan 14 2019) ISSN: 1521-3765 [Electronic] Germany
• PMID: 30351481 (Publication Type: Journal Article)
• Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemical References

• Gangliosides
• Lipopolysaccharides
• Oligosaccharides
• Trisaccharides
• lipid-linked oligosaccharides

Topics

• Campylobacter Infections (complications, pathology)
• Campylobacter jejuni (metabolism)
• Gangliosides (chemistry)
• Glycosylation
• Guillain-Barre Syndrome (etiology, immunology, pathology)
• Humans
• Lipopolysaccharides (chemistry)
• Magnetic Resonance Spectroscopy
• Oligosaccharides (chemical synthesis, chemistry)
• Trisaccharides (chemistry)