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Literature DB >> 27571034

Design and Synthesis of Biaryl DNA-Encoded Libraries.

Yun Ding¹, G Joseph Franklin¹, Jennifer L DeLorey¹, Paolo A Centrella¹, Sibongile Mataruse¹, Matthew A Clark¹, Steven R Skinner¹, Svetlana Belyanskaya¹.

Abstract

DNA-encoded library technology (ELT) is a powerful tool for the discovery of new small-molecule ligands to various protein targets. Here we report the design and synthesis of biaryl DNA-encoded libraries based on the scaffold of 5-formyl 3-iodobenzoic acid. Three reactions on DNA template, acylation, Suzuki-Miyaura coupling and reductive amination, were applied in the library synthesis. The three cycle library of 3.5 million diversity has delivered potent hits for phosphoinositide 3-kinase α (PI3Kα).

Entities: Chemical Gene

Keywords: DNA-encoded library technology; Suzuki−Miyaura cross-coupling

Mesh：

Substances：

Year: 2016 PMID： 27571034 DOI： 10.1021/acscombsci.6b00078

Source DB: PubMed Journal: ACS Comb Sci ISSN： 2156-8944 Impact factor: 3.784

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Cited

13 in total

1. Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support.

Authors: Dillon T Flood; Shota Asai; Xuejing Zhang; Jie Wang; Leonard Yoon; Zoë C Adams; Blythe C Dillingham; Brittany B Sanchez; Julien C Vantourout; Mark E Flanagan; David W Piotrowski; Paul Richardson; Samantha A Green; Ryan A Shenvi; Jason S Chen; Phil S Baran; Philip E Dawson
Journal: J Am Chem Soc Date: 2019-06-12 Impact factor: 15.419

Review 2. Arylation Chemistry for Bioconjugation.

Authors: Chi Zhang; Ekaterina V Vinogradova; Alexander M Spokoyny; Stephen L Buchwald; Bradley L Pentelute
Journal: Angew Chem Int Ed Engl Date: 2019-02-15 Impact factor: 15.336

3. Open-Air Alkylation Reactions in Photoredox-Catalyzed DNA-Encoded Library Synthesis.

Authors: James P Phelan; Simon B Lang; Jaehoon Sim; Simon Berritt; Andrew J Peat; Katelyn Billings; Lijun Fan; Gary A Molander
Journal: J Am Chem Soc Date: 2019-02-12 Impact factor: 15.419

4. On-DNA Reductive Amination and Alkylation.

Authors: Jing Chai
Journal: Methods Mol Biol Date: 2022

5. DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries.

Authors: Vijay Kumar Siripuram; Yashoda Krishna Sunkari; Thu-Lan Nguyen; Marc Flajolet
Journal: Front Chem Date: 2022-06-14 Impact factor: 5.545

Design and Synthesis of Biaryl DNA-Encoded Libraries.

1. Expanding Reactivity in DNA-Encoded Library Synthesis via Reversible Binding of DNA to an Inert Quaternary Ammonium Support.

Review 2. Arylation Chemistry for Bioconjugation.

3. Open-Air Alkylation Reactions in Photoredox-Catalyzed DNA-Encoded Library Synthesis.

4. On-DNA Reductive Amination and Alkylation.

5. DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries.

6. Multifunctional Building Blocks Compatible with Photoredox-Mediated Alkylation for DNA-Encoded Library Synthesis.

Review 7. DNA-Encoded Chemistry: Drug Discovery from a Few Good Reactions.

8. Palladium-Catalyzed Hydroxycarbonylation of (Hetero)aryl Halides for DNA-Encoded Chemical Library Synthesis.

9. Photochemical C-H arylation of heteroarenes for DNA-encoded library synthesis.

Review 10. Impact of Cross-Coupling Reactions in Drug Discovery and Development.