Citation: Nana Yang, Rui Yuan, Xinyue Fu, Xiao Tian, Jin Yu, Shengzhou Ma, Liuqing Wen, Jiabin Zhang. Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy[J]. Chinese Chemical Letters, ;2025, 36(8): 110757. doi: 10.1016/j.cclet.2024.110757 shu

Concise synthesis of NDP-activated uronic acid by an oxidation reaction insertion strategy

Nana Yang ^{b, 1} ,
Rui Yuan ^{a, 1} ,
Xinyue Fu ^{a, b, c} ,
Xiao Tian ^{b, d} ,
Jin Yu ^e ,
Shengzhou Ma ^a ,
Liuqing Wen ^{a, c, *,} ,
Jiabin Zhang ^{a, b, c, *,}

a.
Province Carbohydrate-Based Drug Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
b.
Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, Guangdong 528400, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China
d.
School of Pharmacy, Zunyi Medical University, Zunyi 563006, China
e.
Glycosciences Laboratory, Department of Metabolism, Digestion and Reproduction, Imperial College London, London, W12 0NN, United Kingdom

lwen@simm.ac.cn

jiabinzhang@simm.ac.cn

Received Date: 17 September 2024
Revised Date: 1 December 2024
Accepted Date: 11 December 2024
Available Online: 12 December 2024

Figures(6)

Uronic acids are prevalent components of crucial glycoconjugates, pivotal in various biological processes. In nature, NDP-uronic acids, the nucleosides-activated uronic acids, serve as glycosylation donors catalyzed by uronosyltransferases (UATs) to construct glycans containing uronic acids. Despite their biological importance, the synthesis of naturally occurring NDP-uronic acids on a large scale remains challenging. Here, we developed an oxidation reaction insertion strategy for the efficient synthesis of NDP-uronic acids, and 11 NDP-uronic acids were successfully prepared in good yield and on a large scale. The prepared NDP-uronic acids can be used to explore new uronosyltransferases and synthesize uronic acids containing carbohydrates for fundamental research.
- NDP-uronic acids,
- Biocatalysis,
- Enzyme-mediated biomimetic synthesis,
- Oxidation reaction insertion strategy
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