Chemical Synthesis of Conjugation-Ready Trisaccharides Corresponding to Biological Repeating Units of <i>Pseudomonas aeruginosa</i> Serotype 10 and 19 <i>O</i>-Antigens
Here we report the chemical synthesis of conjugation-ready trisaccharides, representing biological repeating units of <i>Pseudomonas aeruginosa</i> serotype 10 and 19 <i>O</i>-antigens. The α-d-QuiN<sub>3</sub> glycosidic bond was stereoselectively synthesized through TMSI─Ph<sub>3</sub>P═O mediated 1,2-<i>cis</i> glycosylation. Selective oxidation of the C6-OH group at the disaccharide stage allowed for benzylidene-promoted construction of the α-l-GalN<sub>3</sub> 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.
Authors
- Guangzong Tian (ORCID: https://orcid.org/0000-0002-9804-281X)
- Chunjun Qin (ORCID: https://orcid.org/0009-0004-8974-5507)
- Jian Yin (ORCID: https://orcid.org/0000-0002-2284-1666)
- Junxi Zhang
- Xiaopeng Zou
- Jing Hu (ORCID: https://orcid.org/0000-0003-3288-7067)
Institutions
- Jiangnan University (CN)
- Ministry of Education (IR)
- Center for Innovation (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-10-17
- DOI
- https://doi.org/10.1021/acs.orglett.4c03167
- Citations
- 8
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- National Natural Science Foundation of China
- National Key Research and Development Program of China
- Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education