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Metal-free quinolylation of the primary amino groups of amino acid derivatives and peptides with dihydrooxazolo[3,2-a]quinoliniums

文献类型：期刊论文

作者Liu, Peng1,2; Li, Bo1,2; Xi, Mengyu1,2; Chen, Zhaoqiang1,2; Sun, Haiguo1,2; Huan, Xiajuan2; Xu, Xuejun2; Zhang, Yong2; Zou, Kun2; Jiang, Xiangrui1,2
刊名GREEN CHEMISTRY
出版日期2019-08-07
卷号21期号:15页码:4231-4237
ISSN号1463-9262
DOI10.1039/c9gc01442j
通讯作者Li, Bo(boli@simm.ac.cn) ; Zhu, Weiliang(wlzhu@simm.ac.cn)
英文摘要The chemical modification of the primary amino groups of amino acid derivatives and peptides is an important process in the pharmaceutical industry and the field of chemical biology. However, suitable reactions that can be carried out under mild and environmentally friendly conditions are limited. We present a versatile method to selectively modify primary amino groups using novel dihydrooxazolo[3,2-a]quinoliniums in 1-butanol as solvent under mild and metal-free conditions. The application of this method to peptides with primary amino, secondary amino, amide, alcoholic hydroxyl, phenolic hydroxyl, disulfide bond, ester and cyano groups revealed that only the primary amino groups were selectively modified, suggesting that this method is compatible with other reactive moieties. We also demonstrated that the quinolylation of existing peptides affected peptide bioactivity and stability, indicating that the novel dihydrooxazolo[3,2-a]quinoliniums can be widely applied, especially in medicinal chemistry and chemical biology.
WOS关键词TERMINAL PROTEIN MODIFICATION ; DISCOVERY ; TYROSERLEUTIDE ; THERAPEUTICS ; OPTIMIZATION ; OXYTOCIN ; FUTURE
资助项目National Key RD Plan[2016YFA0502301] ; National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China[2018ZX09711002] ; National Natural Science Foundation of China[81573350] ; National Natural Science Foundation of China[81273546] ; National Natural Science Foundation of China[81603270]
WOS研究方向Chemistry ; Science & Technology - Other Topics
语种英语
出版者ROYAL SOC CHEMISTRY
WOS记录号WOS:000484021100026
源URL[http://119.78.100.183/handle/2S10ELR8/288724]  
专题中国科学院上海药物研究所
通讯作者Li, Bo; Zhu, Weiliang
作者单位1.Univ Chinese Acad Sci, Sch Phannacy, 19A Yuquan Rd, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Design Ctr, Key Lab Receptor Res, 555 Zuchongzhi Rd, Shanghai 201203, Peoples R China
3.Pilot Natl Lab Marine Sci & Technol Qingdao, Open Studio Druggabil Res Marine Nat Prod, 1 Wenhai Rd, Qingdao 266237, Shandong, Peoples R China
推荐引用方式
GB/T 7714		 Liu, Peng,Li, Bo,Xi, Mengyu,et al. Metal-free quinolylation of the primary amino groups of amino acid derivatives and peptides with dihydrooxazolo[3,2-a]quinoliniums[J]. GREEN CHEMISTRY,2019,21(15):4231-4237.
APA Liu, Peng.,Li, Bo.,Xi, Mengyu.,Chen, Zhaoqiang.,Sun, Haiguo.,...&Zhu, Weiliang.(2019).Metal-free quinolylation of the primary amino groups of amino acid derivatives and peptides with dihydrooxazolo[3,2-a]quinoliniums.GREEN CHEMISTRY,21(15),4231-4237.
MLA Liu, Peng,et al."Metal-free quinolylation of the primary amino groups of amino acid derivatives and peptides with dihydrooxazolo[3,2-a]quinoliniums".GREEN CHEMISTRY 21.15(2019):4231-4237.

入库方式： OAI收割

来源：上海药物研究所

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