On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis
On-DNA Palladium-Catalyzed Hydrogenation-like Reaction Suitable for DNA-Encoded Library Synthesis
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DOI：
10.1021/acs.bioconjchem.0c00566
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发表时间：
2021-01-20
影响因子：
4.7
通讯作者：
Torrado, Alicia
中科院分区：
文献类型：
--
作者：
Priego, Julian;de Pedro Beato, Eduardo;Torrado, Alicia
本文中，我们描述了一种在其他常见保护基团存在下正交去除DNA上的N-Cbz、N-Alloc、N-AllyL、O-Bn和O-Allyl保护基团以分别得到游离胺和羧酸的方法。所开发的方法使用NaBH 4作为氢源，在Pd（OAc）（2）存在下，在DNA水溶液条件下。此外，在所开发的条件下，我们能够成功地将三键和双键转化为完全饱和的化合物。此外，我们介绍了一种新的替代程序，以减少叠氮化物和芳香族硝基化合物伯胺。
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.