Citation: Juntao Cai, Qian Wang, Xu Shen, Lifeng Zhu, Shiqing Jiang, Jian Yin, Chunhong Dong. Chemical strategies for the stereoselective construction of 1,2-cis-galacturonic and aminogalacturonic acid glycosides[J]. Chinese Chemical Letters, ;2026, 37(5): 112235. doi: 10.1016/j.cclet.2025.112235 shu

Chemical strategies for the stereoselective construction of 1,2-cis-galacturonic and aminogalacturonic acid glycosides

Juntao Cai ^a ,
Qian Wang ^a ,
Xu Shen ^a ,
Lifeng Zhu ^a ,
Shiqing Jiang ^{a, b} ,
Jian Yin ^{c, *,} ,
Chunhong Dong ^{a, *,}

a.
Henan Key Laboratory of Chinese Medicine for Polysaccharides and Drugs Research, Henan University of Chinese Medicine, Zhengzhou 450046, China
b.
Department of Oncology, The First Affiliated Hospital of Henan University of Chinese Medicine, Zhengzhou 450000, China
c.
Key Laboratory of Carbohydrate Chemistry and Biotechnology of Ministry of Education, School of Biotechnology, Jiangnan University, Wuxi 214122, China

jianyin@jiangnan.edu.cn

chunhong_dong@hactcm.edu.cn

Received Date: 23 September 2025
Revised Date: 29 November 2025
Accepted Date: 8 December 2025
Available Online: 9 December 2025

Figures(20)

The stereoselective synthesis of 1,2-cis-galacturonic acid and 2-amino-2-deoxy-galacturonic acid glycosides remains a critical challenge in carbohydrate chemistry owing to the electronic and steric effects imposed by the C5-carboxyl group and C2 substituents. The available synthetic strategies can be divided into two divergent pathways: the construction of the glycan backbone before introducing the carboxyl group and the use of pre-formed uronic acid donors during glycosylation. Key advances include the use of remotely participating acyl groups, conformational control via 3,6-lactone intermediates, chelation-directed anomerisation and steric shielding by bulky protecting groups such as 4,6-O-di-tert-butylsilylene and 4,6-O-benzylidene. This review comprehensively overviews the current strategies that overcome stereo-chemical challenges in the synthesis of 1,2-cis-galacturonic and aminogalacturonic acid–containing glycans. In addition, the application of these methodologies to the synthesis of biologically relevant carbohydrates is examined.
- 1,2-cis-Glycosides,
- Galacturonic acid,
- Aminogalacturonic acid,
- Stereoselective glycosylation,
- Oligosaccharide synthesis,
- Oxidation,
- Uronic acid
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沈阳化工大学材料科学与工程学院沈阳 110142