Chemical synthesis of the O-antigen repeating unit of Actinobacillus actinomycetemcomitans serotype f.
Glycosylation
Lipopolysaccharides (LPS)
O-polysaccharide
Oligosaccharide
One-pot synthesis
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
Dec 2023
Dec 2023
Historique:
received:
06
08
2023
revised:
14
10
2023
accepted:
30
10
2023
medline:
7
12
2023
pubmed:
11
11
2023
entrez:
10
11
2023
Statut:
ppublish
Résumé
Herein, we report the total synthesis of the trisaccharide repeating unit of the O-antigen of Actinobacillus actinomycetemcomitans serotype f. The trisaccharide comprising of α-(1-2) and α-(1-3)-linked L-rhamnopyranosides backbone with the latter rhamnose containing a branching N-acetyl-d-galactosaminopyranoside at the C2-O via a β-glycosidic bond was synthesized by two methods. Initially, the protected trisaccharide has been synthesized by step-wise assembly of the monosaccharide building blocks and subsequently the former was synthesized by the one-pot assembly of the latter components. The synthesized trisaccharide contains an aminoethyl linker appended as an O-glycoside at the reducing end, thereby providing scope for further conjugation for different applications.
Identifiants
pubmed: 37949033
pii: S0008-6215(23)00239-2
doi: 10.1016/j.carres.2023.108977
pii:
doi:
Substances chimiques
O Antigens
0
Monosaccharides
0
Glycosides
0
Trisaccharides
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
108977Informations de copyright
Copyright © 2023 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.