Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy

doi:10.1021/acs.orglett.1c02562

	Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy
	Lin, Bizhen 1; Lu, Weiwei 2; Chen, Zhen-yu 3; Zhang, Yue 1; Duan, Yin-zhe 1; Lu, Xiaojie 2; Yan, Ming 1; Zhang, Xue-jing 1
刊名	ORGANIC LETTERS
	2021-10-01
卷号	23 期号:19 页码:7381-7385
ISSN号	1523-7060
DOI	10.1021/acs.orglett.1c02562
通讯作者	Zhang, Xue-jing(zhangxj33@mail.sysu.edu.cn)
英文摘要	DNA-encoded library (DEL) technology is a powerful tool in the discovery of bioactive probe molecules and drug leads. Mostly, the success in DEL technology stems from the molecular diversity of the chemical libraries. However, the construction of DELs has been restricted by the idiosyncratic needs and the required low concentration (similar to 1 mM or less) of the library intermediate. Here, we report visible-light-promoted on-DNA radical coupling reactions via an electron donor-acceptor (EDA) complex and a reversible adsorption to solid support (BASS) strategy. This protocol provides a unique solution to the challenges of increasing the reactivity of highly diluted DNA substrates and reducing the residues of heavy metals from photocatalysts. A series of on-DNA indole sulfone and selenide derivatives were obtained with good to quantitative conversions. It is anticipated that these mild-condition on-DNA radical reactions will significantly improve the chemical diversity of DELs and find widespread utility to DEL construction.
资助项目	National Natural Science Foundation of China[21772240] ; Fundamental Research Funds for the Central Universities[2021qntd44] ; Natural Science Foundation of Guangdong[2021A1515010503] ; Natural Science Foundation of Guangdong[2021A1515010186] ; Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery[2019B030301005]
WOS关键词	PHOTOREDOX-MEDIATED ALKYLATION ; METAL ; CHEMISTRY ; LIBRARIES
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000704710800013
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/298439]
专题	中国科学院上海药物研究所
通讯作者	Zhang, Xue-jing
作者单位	1.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discover, Guangzhou 510006, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 3.Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China
推荐引用方式 GB/T 7714	Lin, Bizhen,Lu, Weiwei,Chen, Zhen-yu,et al. Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy[J]. ORGANIC LETTERS,2021,23(19):7381-7385.
APA	Lin, Bizhen.,Lu, Weiwei.,Chen, Zhen-yu.,Zhang, Yue.,Duan, Yin-zhe.,...&Zhang, Xue-jing.(2021).Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy.ORGANIC LETTERS,23(19),7381-7385.
MLA	Lin, Bizhen,et al."Enhancing the Potential of Miniature-Scale DNA-Compatible Radical Reactions via an Electron Donor-Acceptor Complex and a Reversible Adsorption to Solid Support Strategy".ORGANIC LETTERS 23.19(2021):7381-7385.