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Chemical Synthesis of Conjugation-Ready Trisaccharides Corresponding to Biological Repeating Units of Pseudomonas aeruginosa Serotype 10 and 19 O -Antigens.
- Source :
-
Organic letters [Org Lett] 2024 Oct 17. Date of Electronic Publication: 2024 Oct 17. - Publication Year :
- 2024
- Publisher :
- Ahead of Print
-
Abstract
- Here we report the chemical synthesis of conjugation-ready trisaccharides, representing biological repeating units of Pseudomonas aeruginosa serotype 10 and 19 O -antigens. The α-d-QuiN <subscript>3</subscript> glycosidic bond was stereoselectively synthesized through TMSI─Ph <subscript>3</subscript> P═O mediated 1,2- cis glycosylation. Selective oxidation of the C6-OH group at the disaccharide stage allowed for benzylidene-promoted construction of the α-l-GalN <subscript>3</subscript> glycosidic bond and simplification of the postglycosylation process at the trisaccharide stage. The low reaction temperature and neighboring electron-donating effect facilitated the efficient synthesis of the trisaccharide.
Details
- Language :
- English
- ISSN :
- 1523-7052
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 39418393
- Full Text :
- https://doi.org/10.1021/acs.orglett.4c03167