Citation: Tian Jiameng, Ning Qianqian, Ding Haixin, Bai Jiang, Xiao Qiang. Synthesis of Enzyme Substrate 6-Chloro-4-methylumbelliferyl-α-L-idopyranosiduronic Acid[J]. Chinese Journal of Organic Chemistry, ;2020, 40(1): 215-220. doi: 10.6023/cjoc201908008 shu

Synthesis of Enzyme Substrate 6-Chloro-4-methylumbelliferyl-α-L-idopyranosiduronic Acid

Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013

Corresponding author: Ding Haixin, dinghaixin_2010@163.com Xiao Qiang, xiaoqiang@tsinghua.org.cn
Received Date: 5 August 2019
Revised Date: 4 September 2019
Available Online: 25 January 2019
Fund Project: the Doctor Startup Fund of Jiangxi Science & Technology Normal University 2018BSQD022Project supported by the National Natural Science Foundation of China (Nos. 21676131, 21462019), the Bureau of Science & Technology of Jiangxi Province (No. 20143ACB20012) and the Doctor Startup Fund of Jiangxi Science & Technology Normal University (No. 2018BSQD022)the National Natural Science Foundation of China 21676131the Bureau of Science & Technology of Jiangxi Province 20143ACB20012the National Natural Science Foundation of China 21462019

Figures(6)

In order to develop fluorogenic enzyme substrate for quick diaganosis of mucopolysaccharidosis type I, 6-chloro-4-methylumbelliferyl-α-L-idopyranosiduronic acid was synthesized from commercially available D-glucurono-6, 3-lactone. Firstly, 1, 2, 3, 4-tetra-O-acetyl-β-D-glucoronate methyl ester was brominated and subsequently reduced with radical reaction to give 1, 2, 3, 4-tetra-O-acetyl-L-idopyranuronate methyl ester. Then 6-chloro-4-methylumbelliferyl-α-L-idopyra-nosiduronic acid was synthesized using Mitsunobu reaction as the key step. The related structures of key intermediates were confirmed with X-ray crystallography. The preliminary biological test proved that the synthesized enzyme substrate could be used for quick detection of α-L-iduronidase.
- α-L-iduronidase,
- fluorogenic enzyme substrate,
- Mitsunobu reaction,
- glycosylation,
- radical reaction
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