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

doi:10.6023/cjoc201908008

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (1): 215-220.DOI: 10.6023/cjoc201908008 Previous Articles Next Articles

糖苷酶底物6-氯-4-甲基伞形酮-α-L-艾杜糖醛酸苷的合成

田加蒙, 宁倩倩, 丁海新, 柏江, 肖强

江西科技师范大学有机功能分子研究所江西省有机功能分子重点实验室南昌 330013

收稿日期:2019-08-05 修回日期:2019-09-04 发布日期:2019-09-25
通讯作者: 丁海新, 肖强 E-mail:dinghaixin_2010@163.com;xiaoqiang@tsinghua.org.cn
基金资助:
国家自然科学基金（Nos.21462019，21676131）、江西省科技厅重点（No.20143ACB20012）和江西科技师范大学博士启动基金（No.2018BSQD022）资助项目.

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

Tian Jiameng, Ning Qianqian, Ding Haixin, Bai Jiang, Xiao Qiang

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

Received:2019-08-05 Revised:2019-09-04 Published:2019-09-25
Supported by:
Project 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).

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Abstract

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.

Key words: α-L-iduronidase, fluorogenic enzyme substrate, Mitsunobu reaction, glycosylation, radical reaction

Cite this article

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.

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糖苷酶底物6-氯-4-甲基伞形酮-α-L-艾杜糖醛酸苷的合成

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

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