Copper(I) in situ-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Long Chain Bifunctional Molecules:Preparation of Biotin Conjugated Glaucocalyxin A Analogs

doi:10.6023/cjoc201903013

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1794-1801.DOI: 10.6023/cjoc201903013 Previous Articles Next Articles

Special Issue: 金属有机化学

Notes

原位Cu(I)催化的叠氮-炔环加成反应合成长链双功能分子:蓝萼甲素与生物素的长链轭合分子的制备

程懂懂^a, 张运晓^a, 王金明^a, 白素平^b

a 郑州大学化学与分子工程学院郑州 450052;
b 新乡医学院药学院新乡 453003

收稿日期:2019-03-07 修回日期:2019-03-28 发布日期:2019-04-16
通讯作者: 张运晓, 白素平 E-mail:zhangyx@zzu.edu.cn;baisuping@xxmu.edu.cn
基金资助:
国家自然科学基金（No.21672182）资助项目.

Copper(I) in situ-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Long Chain Bifunctional Molecules:Preparation of Biotin Conjugated Glaucocalyxin A Analogs

Cheng Dongdong^a, Zhang Yunxiao^a, Wang Jinming^a, Bai Suping^b

a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052;
b College of Pharmacy, Xinxiang Medical University, Xinxiang 453003

Received:2019-03-07 Revised:2019-03-28 Published:2019-04-16
Contact: 10.6023/cjoc201903013 E-mail:zhangyx@zzu.edu.cn;baisuping@xxmu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21672182).

1. Copper(I) in situ-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Long Chain Bifunctional Molecules:Preparation of Biotin Conjugated Glaucocalyxin A Analogs.PDF(4466KB)

Abstract

The novel biotin conjugated glaucocalyxin A analogs as potential activity-based protein probes were synthesized with good yields via Cu(I) in situ-catalyzed azide-alkyne cycloaddition. Cu(I) in situ was good solvated under the optimized condition and shown high catalytic activity. The approach efficiently constructs the even longer linker containing 1,2,3-triazole nucleus between bifunctional groups with the advantages of high regioselectivity and operational simplicity.

Key words: biotin tag, glaucocalyxin A, activity-based probe, Cu(I) in situ catalysis, azide-alkyne cycloaddition

Cite this article

Cheng Dongdong, Zhang Yunxiao, Wang Jinming, Bai Suping. Copper(I) in situ-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Long Chain Bifunctional Molecules:Preparation of Biotin Conjugated Glaucocalyxin A Analogs[J]. Chin. J. Org. Chem., 2019, 39(6): 1794-1801.

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原位Cu(I)催化的叠氮-炔环加成反应合成长链双功能分子:蓝萼甲素与生物素的长链轭合分子的制备

Copper(I) in situ-Catalyzed Azide-Alkyne Cycloaddition in the Synthesis of Long Chain Bifunctional Molecules:Preparation of Biotin Conjugated Glaucocalyxin A Analogs

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