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Systematic Evaluation of On-DNA Nitro Reduction Reactions in Short and Elongated DNA Tags for DNA-Encoded Library Construction.

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Τίτλος: Systematic Evaluation of On-DNA Nitro Reduction Reactions in Short and Elongated DNA Tags for DNA-Encoded Library Construction.
Συγγραφείς: Suh Y; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea., Cho KJ; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea., Kim HJ; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea., Jeon H; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea.
Πηγή: The Journal of organic chemistry [J Org Chem] 2026 Sep 04; Vol. 91 (35), pp. 11916-11922.
Τύπος έκδοσης: Journal Article
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE
Imprint Name(s): Publication: Columbus Oh : American Chemical Society
Original Publication: Easton, Pa. [etc.]
Ιατρικοί όροι (MeSH): DNA*/chemistry , Nitro Compounds*/chemistry , Gene Library*, Oxidation-Reduction
Περίληψη: DNA-encoded library (DEL) synthesis necessitates robust on-DNA chemical transformations that remain dependable throughout multistep library construction, especially for elongated DNA constructs. This study assessed the efficiency of commonly used on-DNA nitro reduction reactions under conditions relevant to practical DEL synthesis to evaluate the impact of DNA tag elongation. Although iron(II)-, diboron-, palladium(II)-, and dithionite-mediated reductions showed high efficiency for short DNA constructs, their performances varied significantly with DNA tag elongation. The generality of these reduction conditions was further explored across a diverse set of nitro-containing substrates, and their chemoselectivities toward additional functional groups were assessed to reflect realistic DEL design considerations. These findings underscore the importance of evaluating on-DNA chemistry beyond minimal tag systems and offer practical guidance for selecting suitable nitro reduction conditions for reliable DEL construction.
(© 2026 American Chemical Society.)
Grant Information: RS-2023-00235550 National Research Foundation of Korea
Substance Nomenclature: 9007-49-2 (DNA)
0 (Nitro Compounds)
Entry Date(s): Date Created: 20260904 Date Completed: 20260904 Latest Revision: 20260904
Update Code: 20260905
DOI: 10.1021/acs.joc.6c00675
PMID: 42695729
Βάση Δεδομένων: MEDLINE
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  Data: Systematic Evaluation of On-DNA Nitro Reduction Reactions in Short and Elongated DNA Tags for DNA-Encoded Library Construction.
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  Data: <searchLink fieldCode="AU" term="%22Suh+Y%22">Suh Y</searchLink>; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea.<br /><searchLink fieldCode="AU" term="%22Cho+KJ%22">Cho KJ</searchLink>; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.<br /><searchLink fieldCode="AU" term="%22Kim+HJ%22">Kim HJ</searchLink>; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea.<br /><searchLink fieldCode="AU" term="%22Jeon+H%22">Jeon H</searchLink>; Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, Daejeon34114, Republic of Korea.; Medicinal Chemistry & Pharmacology, University of Science & Technology, Daejeon34113, Republic of Korea.
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  Data: DNA-encoded library (DEL) synthesis necessitates robust on-DNA chemical transformations that remain dependable throughout multistep library construction, especially for elongated DNA constructs. This study assessed the efficiency of commonly used on-DNA nitro reduction reactions under conditions relevant to practical DEL synthesis to evaluate the impact of DNA tag elongation. Although iron(II)-, diboron-, palladium(II)-, and dithionite-mediated reductions showed high efficiency for short DNA constructs, their performances varied significantly with DNA tag elongation. The generality of these reduction conditions was further explored across a diverse set of nitro-containing substrates, and their chemoselectivities toward additional functional groups were assessed to reflect realistic DEL design considerations. These findings underscore the importance of evaluating on-DNA chemistry beyond minimal tag systems and offer practical guidance for selecting suitable nitro reduction conditions for reliable DEL construction.<br /> (© 2026 American Chemical Society.)
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  Data: RS-2023-00235550 National Research Foundation of Korea
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  Data: 9007-49-2 (DNA)<br />0 (Nitro Compounds)
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        StartPage: 11916
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      – SubjectFull: Oxidation-Reduction
        Type: general
      – SubjectFull: DNA chemistry
        Type: general
      – SubjectFull: Nitro Compounds chemistry
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