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Chamakuri S, Chung MK, Samuel ELG, et al. Design and construction of a stereochemically diverse piperazine-based DNA-encoded chemical library. Bioorg Med Chem. 2021;48:116387doi: 10.1016/j.bmc.2021.116387.
Chamakuri, S., Chung, M. K., Samuel, E. L. G., Tran, K. A., Chen, Y. C., Nyshadham, P., Santini, C., Matzuk, M. M., & Young, D. W. (2021). Design and construction of a stereochemically diverse piperazine-based DNA-encoded chemical library. Bioorganic & medicinal chemistry, 48116387. https://doi.org/10.1016/j.bmc.2021.116387
Chamakuri, Srinivas, et al. "Design and construction of a stereochemically diverse piperazine-based DNA-encoded chemical library." Bioorganic & medicinal chemistry vol. 48 (2021): 116387. doi: https://doi.org/10.1016/j.bmc.2021.116387
Chamakuri S, Chung MK, Samuel ELG, Tran KA, Chen YC, Nyshadham P, Santini C, Matzuk MM, Young DW. Design and construction of a stereochemically diverse piperazine-based DNA-encoded chemical library. Bioorg Med Chem. 2021 Oct 15;48:116387. doi: 10.1016/j.bmc.2021.116387. Epub 2021 Sep 13. PMID: 34571488.
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Bioorg Med Chem. 2021 Oct 15;48:116387. doi: 10.1016/j.bmc.2021.116387. Epub 2021 Sep 13.

Design and construction of a stereochemically diverse piperazine-based DNA-encoded chemical library.

Bioorganic & medicinal chemistry

Srinivas Chamakuri, Mee-Kyung Chung, Errol L G Samuel, Kevin A Tran, Ying-Chu Chen, Pranavanand Nyshadham, Conrad Santini, Martin M Matzuk, Damian W Young

Affiliations

  1. Center for Drug Discovery, Department of Pathology & Immunology, Baylor College of Medicine, Houston, TX 77030, United States. Electronic address: [email protected].
  2. Center for Drug Discovery, Department of Pathology & Immunology, Baylor College of Medicine, Houston, TX 77030, United States.
  3. Department of Pharmacology and Chemical Biology, Baylor College of Medicine, Houston, TX 77030, United States.
  4. Center for Drug Discovery, Department of Pathology & Immunology, Baylor College of Medicine, Houston, TX 77030, United States; Department of Pharmacology and Chemical Biology, Baylor College of Medicine, Houston, TX 77030, United States.
  5. Center for Drug Discovery, Department of Pathology & Immunology, Baylor College of Medicine, Houston, TX 77030, United States; Department of Pharmacology and Chemical Biology, Baylor College of Medicine, Houston, TX 77030, United States; Verna and Marrs McLean Department of Biochemistry and Molecular Biology, Baylor College of Medicine, Houston, TX 77030, United States. Electronic address: [email protected].

PMID: 34571488 DOI: 10.1016/j.bmc.2021.116387

Abstract

Here we report the successful construction of a novel, stereochemically diverse DNA-Encoded Chemical Library (DECL) by utilizing 24 enantiomerically pure trifunctional 2, 6- di-substituted piperazines as central cores. We introduce the concept of positional diversity by placing the DNA attachment at either of two possible sites on the piperazine scaffold. Using a wide range of building blocks, a diverse library of 77 million compounds was produced. Cheminformatic analysis demonstrates that this library occupies a wide swath of chemical space, and that the piperazine scaffolds confers different shape diversity compared to the commonly used triazine core.

Copyright © 2021 Elsevier Ltd. All rights reserved.

Keywords: (sp3) rich compound collection; Encoded chemistry; Piperazines; Stereochemical diversity; Stereogenic compounds

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