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

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...

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Bibliographic Details
Published in:Bioconjugate chemistry 2021-01, Vol.32 (1), p.88-93
Main Authors: Priego, Julián, de Pedro Beato, Eduardo, Benavides, Jesús, Gironda-Martínez, Adrián, González, Fernando, Blas, Jesús, Martín-Ortega, María Dolores, Rama-Garda, Ramón, Ezquerra, Jesús, Toledo, Miguel A, Torrado, Alicia
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Carboxylic acids
Chemical bonds
Deoxyribonucleic acid
DNA
DNA biosynthesis
Nitro compounds
Palladium
Protecting groups
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Summary: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.
ISSN:1043-1802
1520-4812
DOI:10.1021/acs.bioconjchem.0c00566