Total Synthesis of the Trisaccharide Antigen of the Campylobacter jejuni RM1221 Capsular Polysaccharide via de Novo Synthesis of the 6-Deoxy-d- manno-heptose Building Blocks.
J Org Chem
; 84(5): 2393-2403, 2019 03 01.
Article
em En
| MEDLINE
| ID: mdl-30691266
ABSTRACT
A de novo approach utilizing the d-proline-catalyzed and LDA-promoted aldol reactions as key steps for the preparation of differentiated-protected 6-deoxy-d- manno-heptose building blocks was developed. PPh3AuBAr4F-catalyzed glycosylation with the 6-deoxy-d- manno-heptosyl o-hexynylbenzoate as donor was demonstrated as a direct and practical method for the stereoselective synthesis of the ß-linked 6-deoxy-d- manno-heptoside as the major product. Coupling of the 6-deoxy-α-d- manno-heptosyl H-phosphonate with the 3-hydroxyl disaccharide acceptor based on H-phosphonate chemistry was described for the construction of the trisaccharide skeleton with the acid-labile phosphodiester linkage. Finally, first total synthesis of the unique trisaccharide antigen of the capsular polysaccharide of Campylobacter jejuni RM1221 that belongs to HS53 serotype complex was accomplished for further evaluation as vaccine candidate against C. jejuni RM1221 infection.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Polissacarídeos Bacterianos
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Trissacarídeos
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Campylobacter jejuni
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Cápsulas Bacterianas
/
Heptoses
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Antígenos de Bactérias
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
China