Citation: Zijiao Hou, Jianjun Wang, Xinxin Zhang, Peng Wang, Ni Song, Ming Li. Synthesis of a conjugable hexasaccharide corresponding to the capsular polysaccharide of Campylobacter jejuni strain BH0142[J]. Chinese Chemical Letters, ;2023, 34(5): 107804. doi: 10.1016/j.cclet.2022.107804 shu

Synthesis of a conjugable hexasaccharide corresponding to the capsular polysaccharide of Campylobacter jejuni strain BH0142

Zijiao Hou ^a ,
Jianjun Wang ^a ,
Xinxin Zhang ^a ,
Peng Wang ^a ,
Ni Song ^a ,
Ming Li ^{a, b, c, *,}

a.
Molecular Synthesis Center, Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao 266237, China
c.
Shandong Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China

lmsnouc@ouc.edu.cn

Received Date: 8 July 2022
Revised Date: 29 August 2022
Accepted Date: 2 September 2022
Available Online: 6 September 2022

Figures(5)

The first assembly of a conjugation-ready hexasaccharide from the capsular glycan of C. jejuni. strain BH0142 has been accomplished. The synthesis features the efficient preparation of 6-deoxy-d-ido-heptopyranosyl fluoride donors proceeding from allyl α-d-C-glucopyranoside by a C1-to-C5 switch strategy with radical dehydroxymethylative fluorination as a key step, stereocontrolled construction of 1,2-trans-α-d-ido-heptopyranosidic bonds and of 1,2-cis-α-d-galactopyranosidic linkages. The obtained target oligosaccharide sets a solid foundation for making structurally-defined multivalent glycoconjugate vaccine candidates against C. jejuni. infections.
- 6-Deoxy-d-ido-heptopyranosyl fluoride,
- Oligosaccharide synthesis,
- Campylobacter jejuni BH0142,
- Capsular polysaccharide,
- Dehydroxymethylative fluorination,
- Glycosylation
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