Citation: Kebo Xie, Qian Zhang, Fei Ye, Jungui Dai. A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides[J]. Chinese Chemical Letters, ;2024, 35(6): 109028. doi: 10.1016/j.cclet.2023.109028 shu

A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides

Kebo Xie ^*, ,
Qian Zhang ¹ ,
Fei Ye ,
Jungui Dai ^*,

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, CAMS Key Laboratory of Enzyme and Biocatalysis of Natural Drugs and NHC Key Laboratory of Biosynthesis of Natural Products, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

keboxie@imm.ac.cn

jgdai@imm.ac.cn

Received Date: 17 July 2023
Revised Date: 30 August 2023
Accepted Date: 31 August 2023
Available Online: 3 September 2023

Figures(5)

C-Oligosaccharides are rare in nature and possess diverse bioactivities. However, their chemical synthesis faces many challenges. In this work, enzymatic introduction of C-linked sugar chains to target aglycones was successfully achieved by multi-enzymatic cascade reactions. A C-glycosyltransferase from Aloe barbadensis was employed to introduce the first C-linked glucose and then a cyclomaltodextrin glucanotransferase from Bacillus licheniformis was used to extend the sugar chain. A total of twenty C-oligosaccharides with 2–6 sugars were synthesized from scale-up reactions and exhibited good water solubility and sodium-dependent glucose transporter 2 (SGLT2) inhibitory activity. Furthermore, a glucoamylase was used to control the length of the sugar chain and the C-maltosides were efficiently synthesized. These findings not only expanded the structural diversity of C-oligosaccharides, but also provided a strategy for the modification of C-glycoside drugs to improve the druggability.
- C-Oligosaccharides,
- C-Glycosyltransferase,
- Cyclomaltodextrin glucanotransferase,
- Glucoamylase,
- Enzymatic synthesis,
- SGLT2 inhibitory activity
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