化学
合成子
DNA
组合化学
烯丙基重排
酒精氧化
桑格测序
铜
核酸
DNA测序
催化作用
有机化学
生物化学
作者
Justice L. Merrifield,Edward B. Pimentel,Trenton M. Peters-Clarke,Daniel J Nesbitt,Joshua J. Coon,Jeffrey D. Martell
标识
DOI:10.1021/acs.bioconjchem.3c00254
摘要
Aldehydes are important synthons for DNA-encoded library (DEL) construction, but the development of a DNA-compatible method for the oxidation of alcohols to aldehydes remains a significant challenge in the field of DEL chemistry. We report that a copper/TEMPO catalyst system enables the solution-phase DNA-compatible oxidation of DNA-linked primary activated alcohols to aldehydes. The semiaqueous, room-temperature reaction conditions afford oxidation of benzylic, heterobenzylic, and allylic alcohols in high yield, with DNA compatibility verified by mass spectrometry, qPCR, Sanger sequencing, and ligation assays. Subsequent transformations of the resulting aldehydes demonstrate the potential of this method for robust library diversification.
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