DNA Compatible Intermolecular Wittig Olefination for the Construction of α, β‑Unsaturated Carbonyl Compounds

A robust DNA-compatible Wittig reaction mediated by PPh2CH3 has been validated for DNA-conjugated α-chloroacetamides with aldehydes and, alternatively, DNA-conjugated aldehydes with α-halo acetamides or ketones. Further, 2-aminopyridines were acylated with α-chloroacetyl chloride and then reacted wi...

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Published inOrganic letters Vol. 22; no. 10; pp. 3931 - 3935
Main Authors An, Yu-Long, Li, Ke, Shen, Yanfang, Hong, Zibing, Chen, Linlin, Hu, Yujing, Zhou, Lichun, Wang, Disha, Shi, Xiaodong, Liu, Shien, Su, Wenji, Cui, Weiren, Kuai, Letian, Yang, Hongfang, Peng, Xuanjia
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 15.05.2020
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Summary:A robust DNA-compatible Wittig reaction mediated by PPh2CH3 has been validated for DNA-conjugated α-chloroacetamides with aldehydes and, alternatively, DNA-conjugated aldehydes with α-halo acetamides or ketones. Further, 2-aminopyridines were acylated with α-chloroacetyl chloride and then reacted with DNA-conjugated aldehydes. Lastly, a pilot library employing our optimized Wittig reaction protocol was synthesized. The ability to generate α,β-unsaturated carbonyl compounds may be particularly useful for the design of DNA-encoded libraries capable of covalently interacting with protein targets.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01215