On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis,Bioconjugate Chemistry

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On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2020-12-24 , DOI: 10.1021/acs.bioconjchem.0c00566
Julián Priego ₁ , Eduardo de Pedro Beato ₁ , Jesús Benavides ₁ , Adrián Gironda-Martínez ₁ , Fernando González ₁ , Jesús Blas ₁ , María Dolores Martín-Ortega ₁ , Ramón Rama-Garda ₁ , Jesús Ezquerra ₁ , Miguel A Toledo ₁ , Alicia Torrado ₁

Affiliation

Herein we describe a method to orthogonally remove on-DNA N-Cbz, N-Alloc, N-Allyl, O-Bn, and O-Allyl protecting groups in the presence of other common protecting groups to afford free amines and carboxylic acids, respectively. The developed method uses NaBH₄ as the source of hydrogen in the presence of Pd(OAc)₂ under DNA aqueous conditions. In addition, under the developed conditions we were able to successfully hydrogenate triple and double bonds to totally saturated compounds. Furthermore, we introduce a new alternative procedure to reduce azides and aromatic nitro compounds to primary amines.

中文翻译：

适用于 DNA 编码文库合成的 On-DNA 钯催化类氢化反应

本文中，我们描述到正交去除-DNA的方法Ñ -Cbz，Ñ -alloc，Ñ分别烯丙基，O- BN，和O-烯丙基的保护基团中其它常见的保护基团，得到游离胺和羧酸的存在下， . 所开发的方法在 DNA 水溶液条件下，在 Pd(OAc) ₂存在下，使用 NaBH ₄作为氢源。此外，在开发的条件下，我们能够成功地将三键和双键氢化成完全饱和的化合物。此外，我们引入了一种新的替代方法，将叠氮化物和芳香族硝基化合物还原为伯胺。

更新日期：2021-01-20

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