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

被引：7

作者：

Priego, Julian ^{[1
]}

de Pedro Beato, Eduardo ^{[1
]}

Benavides, Jesus ^{[1
]}

Gironda-Martinez, Adrian ^{[1
]}

Gonzalez, Fernando ^{[1
]}

Blas, Jesus ^{[1
]}

Dolores Martin-Ortega, Maria ^{[1
]}

Rama-Garda, Ramon ^{[1
]}

Ezquerra, Jesus ^{[1
]}

Toledo, Miguel A. ^{[1
]}

Torrado, Alicia ^{[1
]}

机构：

[1] Ctr Invest Lilly SA, Madrid 28108, Spain

来源：

BIOCONJUGATE CHEMISTRY | 2021年 / 32卷 / 01期

关键词：

REDUCTION;

D O I：

10.1021/acs.bioconjchem.0c00566

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：88 / 93

页数：6

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