DNA-Compatible Copper-Catalyzed Oxidative Amidation of Aldehydes with Non-Nucleophilic Arylamines.


Journal

Bioconjugate chemistry
ISSN: 1520-4812
Titre abrégé: Bioconjug Chem
Pays: United States
ID NLM: 9010319

Informations de publication

Date de publication:
16 09 2020
Historique:
pubmed: 18 8 2020
medline: 22 6 2021
entrez: 18 8 2020
Statut: ppublish

Résumé

We report a DNA-compatible protocol for synthesizing amides from DNA-bound aldehydes and non-nucleophilic arylamines including aza-substituted anilines, 2-aminobenzimidazoles, and 3-aminopyrazoles. The reactions were carried out at room temperature and provided reasonable conversions and wide functional group compatibility. The reactions were also successful when employing aryl and aliphatic aldehydes. In addition, qPCR and NGS data suggested no negative impact on DNA integrity after the copper-mediated oxidative amidation reaction.

Identifiants

pubmed: 32804494
doi: 10.1021/acs.bioconjchem.0c00392
doi:

Substances chimiques

Aldehydes 0
Amides 0
Amines 0
Aniline Compounds 0
Copper 789U1901C5
DNA 9007-49-2

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

2092-2097

Auteurs

Ke Li (K)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Yi Qu (Y)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Yulong An (Y)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Eric Breinlinger (E)

AbbVie Bioresearch Center, 381 Plantation Street, Worcester, Massachusetts 01605, United States.

Matthew P Webster (MP)

Research and Development, AbbVie, 1 North Waukegan Road, North Chicago, Illinois 60064, United States.

Huanan Wen (H)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Duanchen Ding (D)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Meng Zhao (M)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Xiaodong Shi (X)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Jiangong Wang (J)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Wenji Su (W)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Weiren Cui (W)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Alexander L Satz (AL)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Hongfang Yang (H)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Letian Kuai (L)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

Andrew Little (A)

AbbVie Bioresearch Center, 381 Plantation Street, Worcester, Massachusetts 01605, United States.

Xuanjia Peng (X)

WuXi AppTec (Shanghai) Co., Ltd. 288 Middle Fu Te Road, Shanghai 200131, China.

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Classifications MeSH