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  Chemical synthesis elucidates the key antigenic epitope of the autism-related bacterium Clostridium bolteae capsular octadecasaccharide

Cai, J., Hu, J., Qin, C., Li, L., Shen, D., Tian, G., et al. (2020). Chemical synthesis elucidates the key antigenic epitope of the autism-related bacterium Clostridium bolteae capsular octadecasaccharide. Angewandte Chemie International Edition, 59(46), 20529-20537. doi:10.1002/anie.202007209.

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 Creators:
Cai, Juntao, Author
Hu, Jing, Author
Qin, Chunjun, Author
Li, Lingxin, Author
Shen, Dacheng1, Author           
Tian, Guangzong, Author
Zou, Xiaopeng, Author
Seeberger, Peter H.1, Author           
Yin, Jian, Author
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              

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Free keywords: Clostridium bolteae, immunology, capsular polysaccharide, total synthesis, octadecasaccharide
 Abstract: The gut pathogen Clostridium bolteae has been associated with the onset of autism spectrum disorder (ASD). To create vaccines against C. bolteae, it is important to identify exact protective epitopes of the immunologically active capsular polysaccharide (CPS). Here, we prepared a series of C. bolteae CPS glycans up to an octadecasaccharide. Key to achieving the total syntheses is a [2+2] coupling strategy based on a ß-d-Rha p -(1→3)-α-d-Man p repeating unit that in turn was accessed via a stereoselective ß-d-rhamnosylation. The 4,6- O -benzylidene-induced conformational locking is a powerful strategy for forming ß-d-mannose-type glycoside. An indirect strategy based on the C2 epimerization of ß-d-quinovoside was efficiently achieved by Swern oxidation and borohydride reduction. Sequential glycosylation, regioselective and global deprotection produced disaccharide, tetrasaccharide, all the way to octadecasaccharide. Glycan microarrays analysis of sera from rabbits immunized with inactivated C. bolteae bacteria revealed a humoral immune response to di- and tetrasaccharide but none of the longer sequences. Tetrasaccharide may be a key motif for designing glycoconjugate vaccines against C. bolteae .

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Language(s): eng - English
 Dates: 2020-07-312020
 Publication Status: Published in print
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (46) Sequence Number: - Start / End Page: 20529 - 20537 Identifier: ISSN: 1433-7851

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Title: Angewandte Chemie
  Abbreviation : Angew. Chem.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 132 (46) Sequence Number: - Start / End Page: 20710 - 20718 Identifier: ISSN: 0044-8249