Conformationally Restricted GalN3 Donors Enable Zinc(II)-Mediated Stereocontrolled Galactosylation
Abstract We report a Zn(II)-mediated stereocontrolled galactosylation with two conformationally restricted GalN3 donors that enables divergent α- and β-glycosylation. The 4,6-O-TIPDS/3-O-Bz donor selectively affords α-GalN3 glycosides, while the 4,6-O-benzylidene/3-O-TIPS donor provides β-glycosides with high stereoselectivity. The methods show a broad substrate scope, good yields, and scalability and enable synthesis of GalNAc-α-Ser and the Acinetobacter baumannii CPS K45 tetrasaccharide repeating unit.
Authors
- Hui Cai (ORCID: https://orcid.org/0000-0002-5394-8167)
- 郭向彤
- Siai Zhou (ORCID: https://orcid.org/0009-0000-6057-5349)
- Feiqing Ding (ORCID: https://orcid.org/0000-0002-0211-7101)
- Jiawei Li (ORCID: https://orcid.org/0000-0001-5646-198X)
- Lan Ye
- Guoqing Wang
Institutions
- Sun Yat-sen University (CN)
- The Seventh Affiliated Hospital of Sun Yat-sen University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-15
- DOI
- https://doi.org/10.1021/acs.orglett.6c03888
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Guangdong Province
- Science and Technology Planning Project of Guangdong Province
- Science and Technology Planning Project of Shenzhen Municipality
- Shenzhen Science and Technology Innovation Program