4.8 Article

The Components of xRNA: Synthesis and Fluorescence of a Full Genetic Set of Size-Expanded Ribonucleosides

期刊

ORGANIC LETTERS
卷 13, 期 4, 页码 676-679

出版社

AMER CHEMICAL SOC
DOI: 10.1021/ol102915f

关键词

-

资金

  1. National Institutes of Health [GM063587, GM084680]

向作者/读者索取更多资源

The synthesis and properties of a full set of four benzo-expanded ribonucleosides (xRNA), analogous to A, G, C, and U RNA monomers, are described. The nucleosides are efficient fluorophores with emission maxima of 369-411 nm. The compounds are expected to be useful as RNA pathway probes and as components of an unnatural ribopolymer.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Article Chemistry, Multidisciplinary

Fluorescence Imaging of Mitochondrial DNA Base Excision Repair Reveals Dynamics of Oxidative Stress Responses

Yong Woong Jun, Eddy Albarran, David L. Wilson, Jun Ding, Eric T. Kool

Summary: Mitochondrial function declines with aging and neurodegeneration, largely due to accumulated mutations in mtDNA from deficient DNA repair. A fluorescent probe, UBER, was used to visualize mitochondrial BER activity, showing increased repair under oxidative stress and time delay between stress onset and BER initiation. Cells lacking MTH1 exhibited elevated demand for BER activity during extended stress, while absence of OGG1 limited glycosylation capacity.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

Article Chemistry, Multidisciplinary

Conjugation of RNA via 2′-OH acylation: Mechanisms determining nucleotide reactivity

Biswarup Jash, Eric T. Kool

Summary: In this study, we investigated the acylation reactivity of RNA 2'-OH groups and identified the strong influence of steric and inductive effects on the reaction. These findings provide insights into new strategies for enhancing conjugation and mapping of RNA.

CHEMICAL COMMUNICATIONS (2022)

Article Microbiology

Microbial byproducts determine reproductive fitness of free-living and parasitic nematodes

Mericien Venzon, Ritika Das, Daniel J. Luciano, Julia Burnett, Hyun Shin Park, Joseph Cooper Devlin, Eric T. Kool, Joel G. Belasco, E. Jane Albert Hubbard, Ken Cadwell

Summary: Microbial byproducts play a crucial role in the reproductive development of nematodes by affecting their fertility and hatching abilities through alterations in arginine and aldehyde levels.

CELL HOST & MICROBE (2022)

Meeting Abstract Biochemistry & Molecular Biology

Fluorescent detection of RNA using a base excision reporter

Emily M. Harcourt, Yong Woong Jun, David L. Wilson, Emily D. Ledgerwood, Eric T. Kool

FASEB JOURNAL (2022)

Article Biochemistry & Molecular Biology

Enhancing Repair of Oxidative DNA Damage with Small-Molecule Activators of MTH1

Yujeong Lee, Yoshiyuki Onishi, Lisa McPherson, Anna M. Kietrys, Marian Hebenbrock, Yong Woong Jun, Ishani Das, Shanthi Adimoolam, Debin Ji, Michael G. Mohsen, James M. Ford, Eric T. Kool

Summary: Impaired DNA repair activity is associated with increased cancer rates. This study found that certain tyrosine kinase inhibitors, such as nilotinib, can activate the repair enzyme MTH1, which cleanses oxidatively damaged nucleotides. Structural optimization resulted in compounds that strongly activate MTH1 and decrease mutagenic nucleotides in cellular DNA. These findings suggest that MTH1 activators may be a promising strategy to suppress tumorigenesis in individuals with elevated cancer risks.

ACS CHEMICAL BIOLOGY (2022)

Article Multidisciplinary Sciences

Efficient DNA fluorescence labeling via base excision trapping

Yong Woong Jun, Emily M. Harcourt, Lu Xiao, David L. Wilson, Eric T. Kool

Summary: This article presents a convenient and versatile method for general fluorescence labeling of DNAs. It utilizes deaminated DNA bases and aminooxy-substituted rotor dyes to mark label positions and trap AP sites, resulting in high emission intensities for fluorescence labeling of oligonucleotides and dsDNA.

NATURE COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Chemical Tools for the Study of DNA Repair

Yong Woong Jun, Eric T. Kool

Summary: DNA repair enzymes play a significant role in protecting cellular DNA from damage and are closely associated with cancer and inflammation pathways. The development of new tools and methods has greatly contributed to the study of these enzymes and their potential applications in diagnostics and therapies. This article provides an overview of the development of chemical tools for studying DNA repair processes and discusses the insights gained from their application. The article also highlights the importance of future research in the field of biomedicine and human health.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

Article Chemistry, Multidisciplinary

Diverse Reagent Scaffolds Provide Differential Selectivity of 2'-OH Acylation in RNA

Lu Xiao, Linglan Fang, Sayantan Chatterjee, Eric T. Kool

Summary: RNA 2'-OH acylation is widely used for structure mapping and conjugation, and depends on selective reactions with unpaired nucleotides. We prepared a range of structurally diverse acylimidazole reagents and used deep sequencing to study their reactivity and selectivity in a variety of RNA structures. Our results demonstrate that the reagent scaffold significantly affects reactivity profiles and highlight new acylating agents with altered selectivity, including compounds that show elevated selectivity within loops and reduced off-target reactivity in loop closing base pairs. We also discovered a simple reagent that is cell permeable and can map RNA structure in the presence of protein contacts, and describe reagents with elevated selectivity within small loops for site-selective labeling.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2023)

Article Chemistry, Multidisciplinary

Sulfonylation of RNA 2′-OH groups

Sayantan Chatterjee, Ryuta Shioi, Eric T. Kool

Summary: The nucleophilic reactivity of RNA 2'-OH groups has been applied in various RNA-related processes. In this study, it is discovered that activated small-molecule sulfonyl species can retain their reactivity in water. Reactions with ribose 2'-OH show high yields, especially for aryl sulfonyltriazole species. Additionally, an azide-substituted sulfonyltriazole reagent is developed for labeling RNA via click chemistry.

ACS CENTRAL SCIENCE (2023)

Article Chemistry, Multidisciplinary

Possible Genetic Risks from Heat-Damaged DNA in Food

Yong Woong Jun, Melis Kant, Erdem Coskun, Takamitsu A. A. Kato, Pawel Jaruga, Elizabeth Palafox, Miral Dizdaroglu, Eric T. T. Kool

Summary: High-temperature cooking damages DNA in food, which can then enter the cellular DNA and lead to genetic risks.

ACS CENTRAL SCIENCE (2023)

Article Chemistry, Multidisciplinary

Reversible 2′-OH acylation enhances RNA stability

Linglan Fang, Lu Xiao, Yong Woong Jun, Yoshiyuki Onishi, Eric T. T. Kool

Summary: The presence of a hydroxyl group at the 2'-position in ribose makes RNA susceptible to hydrolysis. In this study, reversible 2'-OH acylation was presented as a general strategy to preserve RNA stability. High-yield polyacylation of 2'-hydroxyls effectively protected RNAs from degradation, and subsequent treatment with nucleophilic reagents removed acylation adducts and recovered a wide range of RNA functions.

NATURE CHEMISTRY (2023)

Article Chemistry, Multidisciplinary

Stereoselective RNA reaction with chiral 2′-OH acylating agents

Ryuta Shioi, Lu Xiao, Sayantan Chatterjee, Eric T. Kool

Summary: The reactivity of RNA 2'-OH groups with acylating agents has been studied for high-yield conjugation of RNA strands. This study focuses on the stereoselectivity of chiral acylimidazoles in RNA reactions. The results reveal that positional selectivity and reactivity vary greatly with local RNA macro-chirality, and the chirality of the reagents has a significant impact on their reactivity. This study demonstrates new chemical strategies for selective RNA modification and probing.

CHEMICAL SCIENCE (2023)

Article Biochemical Research Methods

Integrating transcription-factor abundance with chromatin accessibility in human erythroid lineage commitment

Reema Baskar, Amy F. Chen, Patricia Favaro, Warren Reynolds, Fabian Mueller, Luciene Borges, Sizun Jiang, Hyun Shin Park, Eric T. Kool, William J. Greenleaf, Sean C. Bendall

Summary: Master transcription factors regulate cell states by driving gene-expression programs, and their abundance affects cell fate at the chromatin level. InTAC-seq method allows the study of the relationship between protein abundance and gene regulation in cells.

CELL REPORTS METHODS (2022)

Article Biochemistry & Molecular Biology

Acylation probing of genericRNA libraries reveals critical influence of loop constraints on reactivity

Lu Xiao, Linglan Fang, Eric T. Kool

Summary: The reactivity of RNA 2'-OH acylation has been extensively studied in this research. The results show that there is a wide range of reactivity among single-stranded RNA sequences, with nearest neighbors playing a significant role. Interestingly, certain small loops exhibit much higher reactivity compared to single-stranded RNAs, which is attributed to conformational constraints.

CELL CHEMICAL BIOLOGY (2022)

Article Chemistry, Multidisciplinary

Mechanism-Based Strategy for Optimizing HaloTag Protein Labeling

Sergio M. Marques, Michaela Slanska, Klaudia Chmelova, Radka Chaloupkova, Martin Marek, Spencer Clark, Jiri Damborsky, Eric T. Kool, David Bodnar, Zbynek Prokop

Summary: HaloTag labeling technology has revolutionized protein chemistry and cellular biology, and a systematic analysis of different ligands has led to the discovery of an optimal protein tag selection protocol, eliminating the need for expensive and complex protein engineering.

JACS AU (2022)

暂无数据