Improvement of Kdo's efficient large-scale chemical synthesis method

doi:10.5246/jcps.2022.02.008

Journal of Chinese Pharmaceutical Sciences ›› 2022, Vol. 31 ›› Issue (2): 97-107.DOI: 10.5246/jcps.2022.02.008

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Improvement of Kdo's efficient large-scale chemical synthesis method

Ao Sun, Zipeng Li, Ting Liu, Xiangbao Meng, Shuchun Li^*(), Zhongjun Li^*()

The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2021-10-25 Revised:2021-11-17 Accepted:2021-11-29 Online:2022-02-27 Published:2022-02-25
Contact: Shuchun Li, Zhongjun Li

Abstract

Abstract:

Kdo residues are widely distributed in bacteria. They are components of bacterial lipopolysaccharide (LPS) and capsular polysaccharides, which can be recognized by the human adaptive immune system, and have great potential for developing new sugar chips and antibacterial vaccines. By improving the existing methods, we optimized the Kdo chemical synthesis method, which was able to efficiently synthesize Kdo monosaccharides with high purity, laying a foundation for the construction of subsequent compound libraries. Kdo acylation can easily form 1,5-lactones and reduce the efficiency of synthesis. By changing the synthesis sequence, we avoided the formation of Kdo 1,5-lactones, improved the synthesis efficiency of Kdo glycals, and provided a new strategy for derivatization.

Key words: Kdo, Chemical synthesis, 1,5-Lactone, Glycal

Supporting:

Ao Sun, Zipeng Li, Ting Liu, Xiangbao Meng, Shuchun Li, Zhongjun Li. Improvement of Kdo's efficient large-scale chemical synthesis method[J]. Journal of Chinese Pharmaceutical Sciences, 2022, 31(2): 97-107.

Figures/Tables 5

References 18

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Improvement of Kdo's efficient large-scale chemical synthesis method

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