钯介导的 Boc-保护的氨甲基三氟硼酸钾与 DNA 连接的芳基溴的 Suzuki-Miyaura 交叉偶联反应用于 DNA 编码的化学文库合成。
Palladium-mediated Suzuki-Miyaura Cross-Coupling Reaction of Potassium Boc-protected aminomethyltrifluoroborate with DNA-Conjugated aryl bromides for DNA-Encoded chemical library synthesis.
机构信息
DNA Encoded Library Platform, WuXi AppTec, 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai, 200131, China.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Zhang Jiang Hi-Tech Park, Pudong, Shanghai, 201203, PR China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing, 100049, China.
出版信息
Biochem Biophys Res Commun. 2020 Dec 3;533(2):209-214. doi: 10.1016/j.bbrc.2020.04.027. Epub 2020 May 4.
A mild reaction for DNA-compatible, palladium promoted Suzuki-Miyaura cross-coupling reaction of potassium Boc-protected aminomethyltrifluoroborate with DNA-conjugated aryl bromides has been developed efficiently. This novel DNA encoded chemistry reaction proceeded well with a wide range of functional group tolerance, including aryl bromides and heteroaryl bromides. Further, the utility our DNA conjugated aminomethylated arene products is demonstrated by reaction with various types of reagents (including amide formation with carboxylic acids, alkylation with aldehydes, and carbamoylation with amines) as would be desired for the production of a DNA encoded library.
发展了一种对 DNA 相容的、钯促进的 Boc 保护的氨甲基三氟硼酸钾与 DNA 键合的芳基溴的 Suzuki-Miyaura 交叉偶联反应的温和反应条件。这种新颖的 DNA 编码化学反应用于广泛的官能团容忍性，包括芳基溴化物和杂芳基溴化物，效果很好。此外，通过与各种类型的试剂（包括与羧酸形成酰胺、与醛烷基化和与胺形成氨基甲酰化）反应，证明了我们的 DNA 键合氨甲基芳烃产物的实用性，这是构建 DNA 编码文库所需要的。
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