Chemical pulldown of Prenylated-Adenosine-Incorporated RNA via sequential Fluorination-Azidation and a click reaction targeting prenyl functionality

Chen, Xiaoqian; Gan, Youfang; Guo, Yuyang; Li, Yuanyuan; Zhou, Hongling; Wang, Rui

doi:10.1016/j.tetlet.2023.154856

Cited by 2 publications

(1 citation statement)

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“…Our study commenced with an investigation into novel biorthogonal transformations involving the N 6 -isopentenyl substituent, [34][35][36][37] specifically the 1,1,2-trisubstituted double bond (Scheme 2). While alkenes are versatile building blocks in synthetic chemistry due to their diverse reactions as valuable intermediates in substitution, addition, and other reactions, multi-substituted alkenes pose challenges in many transformations owing to their significant steric hindrance, resulting in reduced reactivity.…”

Section: Resultsmentioning

confidence: 99%

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA

Sun,

Hui,

Liu

et al. 2024

ChemBioChem

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RNA modifications play crucial roles in regulating gene expression and cellular homeostasis. Modulating RNA modifications, particularly by targeting the enzymes responsible for their catalysis, has emerged as a promising therapeutic strategy. However, limitations, such as the lack of identified modifying enzymes and compensatory mechanisms, hinder targeted interventions. Chemical approaches independent of enzymatic activity offer an alternative strategy for RNA modification modulation. Here, we present the identification of 2‐chloro‐3,5‐dinitrobenzoic acid as a highly effective photochemical deprenylase of i6A RNA. This method demonstrates exceptional selectivity towards i6A, converting its substituent into a "N‐doped" ozonide, which upon hydrolysis releases natural adenine. We believe that this chemical approach will pave the way for a better understanding of RNA modification biology and the development of novel therapeutic modalities.

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Section: Resultsmentioning

confidence: 99%

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA

Sun,

Hui,

Liu

et al. 2024

ChemBioChem

View full text Add to dashboard Cite

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Advances in the investigation of N6-isopentenyl adenosine i6A RNA modification

Lin,

Gai,

Liu

et al. 2024

Bioorganic & Medicinal Chemistry

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Chemical pulldown of Prenylated-Adenosine-Incorporated RNA via sequential Fluorination-Azidation and a click reaction targeting prenyl functionality

Cited by 2 publications

References 32 publications

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA

Advances in the investigation of N6-isopentenyl adenosine i6A RNA modification

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Chemical pulldown of Prenylated-Adenosine-Incorporated RNA via sequential Fluorination-Azidation and a click reaction targeting prenyl functionality

Cited by 2 publications

References 32 publications

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i6A RNA

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i6A RNA

Advances in the investigation of N6-isopentenyl adenosine i6A RNA modification

Contact Info

Product

Resources

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Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA

Discovery of Photoexcited 2‐Chloro‐3,5‐Dinitrobenzoic Acid as a Chemical Deprenylase of i⁶A RNA