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

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外文摘要：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 bar-badensis was employed to introduce the first C-linked glucose and then a cyclomaltodextrin glucanotrans-ferase 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.

外文关键词：

C-OligosaccharidesC-GlycosyltransferaseCyclomaltodextrin glucanotransferaseGlucoamylaseEnzymatic synthesisSGLT2 inhibitory activity

作者：

Kebo Xie、Qian Zhang、Fei Ye、Jungui Dai

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作者单位：

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

基金：

National Key Research and Development Program of ChinaCAMS Innovation fund for Medical Sciences

项目编号：

2020YFA09080002021-I2M-1-029

出版年：

2024

DOI：

10.1016/j.cclet.2023.109028

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCD

影响因子：0.771

ISSN：1001-8417

年,卷(期)：2024.35(6)