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AgOTf-Assisted β-Glucuronidation Enables Convergent Synthesis of β-(1 → 4)-Linked Polyglucuronates up to the 32-Mer
Xinyang Jiang1,2, Can Jin1, Peifan Xu1,3
1Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan528400, China.
Journal of the American Chemical Society
|August 12, 2026
Summary
This study introduces a novel gold(I)-catalyzed method for synthesizing beta-glucuronides, overcoming previous limitations in glucuronidation. The new approach enables efficient construction of complex molecules, including long-chain polyglucuronates.
Area of Science:
- Carbohydrate Chemistry
- Organometallic Catalysis
- Glycobiology
Background:
- Beta-glucuronides are crucial in biological systems but challenging to synthesize due to the low reactivity of glucuronic acid.
- Existing methods for glucuronidation often suffer from low yields and limited substrate scope.
Purpose of the Study:
- To develop a robust and general method for beta-glucuronidation using gold(I) catalysis.
- To enable the synthesis of complex glucuronides and polyglucuronates.
Main Methods:
- Utilized glucuronosyl 8-alkynyl-1-naphthoate donors with gold(I) and silver triflate (AgOTf) catalysis.
- Investigated the reaction mechanism, including the roles of AgOTf and in situ generated HOTf.
- Demonstrated compatibility with various protecting groups and electron-withdrawing substituents.
Main Results:
- Achieved efficient beta-glucuronidation using the novel gold(I)-catalyzed system.
- Elucidated the catalytic cycle involving AgOTf and HOTf.
- Successfully synthesized a 32-mer of beta-(1 -> 4)-polyglucuronate (glucuronan).
Conclusions:
- The developed gold(I)-catalyzed method provides a versatile platform for beta-glucuronide synthesis.
- This breakthrough facilitates the construction of challenging anionic polysaccharides like glucuronan.
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