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An unprecedented synthesis of axially chiral biaryls by rearrangement and aromatization of carbocations with central-to-axial conversion of chirality

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Science China Chemistry 2024年第9期67卷 2998-3003页

作者： Qi Liu Xue-Dong Li Liang Cheng Li Liu Beijing National Laboratory for Molecular Sciences(BNLMS) CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular SciencesInstitute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China

The central-to-axial chirality conversion represents a fascinating class of chemical processes consisting of the destruction of stereogenic centers and the simultaneous installation of axial chiral elements,which provides efficient methods for the preparation of axially chiral ***,developing catalytic asymmetric approaches for constructing these central chirality precursors and the efficient central-to-axial chirality conversion remains a challenge due to the requirement of aromatization or elimination *** this work,we have developed an unprecedented enantioselective intramolecular FriedelCrafts alkylation with unactivated-ketone carbonyls from which a chiral tertiary alcohol was generated with high efficiency and excellent *** addition,the central-to-axial chirality conversion strategy has been successfully applied to the synthesis of enantioenriched biaryls via a less-explored carbocation-initiated rearrangement and aromatization under the promotion of Lewis *** methodology provided a straightforward and sustainable access to a broad range of biaryl-2-carboxylic acid and in excellent yields(up to 92%)and excellent central-to-axial chirality conversion(up to 99%conversion percentage).This work could be a great model for developing new methods for synthesizing axially chiral biaryls and a general protocol for the rearrangement and aromatization of carbocations for further functionalization.

关键词： br?nsted acid catalysis desymmetrization phosphoric acid axially chiral biaryls central-to-axial conversion

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N^(4)-乙酰胞苷RNA检测技术的研究进展

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高等学校化学学报 2023年第3期44卷 167-174页

作者：贺胤铭孔素东林建国谢敏浩程靓中国科学院化学研究所北京分子科学国家研究中心中国科学院分子科学科教融合卓越创新中心分子识别与功能重点实验室北京100190 江南大学化学与材料工程学院无锡214122 国家卫生健康委员会核医学重点实验室江苏省原子医学研究所无锡214063 中国科学院大学北京100049

细胞中的mRNA和非编码RNA包含着大量的表观化学修饰.在这些修饰中,N^(4)-乙酰胞苷(ac^(4)C)是较为独特的一种,在真核生物和原核生物的tRNA,rRNA和mRNA中均有发现.研究表明,ac^(4)C RNA可能具有多种生物学功能,包括调节蛋白的翻译过程、... 详细信息

细胞中的mRNA和非编码RNA包含着大量的表观化学修饰.在这些修饰中,N^(4)-乙酰胞苷(ac^(4)C)是较为独特的一种,在真核生物和原核生物的tRNA,rRNA和mRNA中均有发现.研究表明,ac^(4)C RNA可能具有多种生物学功能,包括调节蛋白的翻译过程、影响RNA的稳定性及改变RNA-蛋白相互作用等.但当前对其修饰路径的研究还不成熟,催化ac^(4)C RNA形成的乙酰转移酶目前仅有NAT10被鉴定出来.不仅如此,目前对ac^(4)C RNA进行检测和测序的技术手段还相当局限.本文综合评述了ac^(4)C RNA的分布以及在基因表达调控中的作用和机制,重点介绍了ac^(4)C RNA的检测技术,并对ac^(4)C RNA当前研究中的不足和机遇进行了总结和展望.

关键词： N4-乙酰胞苷 RNA修饰检测方法

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A Bioorthogonal Post-modification of N^(6)-Isopentenyl Adenosine i^(6) A RNA in Live Cells

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CCS Chemistry 2024年第9期6卷 2241-2253页

作者： Li-Jun Xie Hou-Ping Cheng Meng-Yuan Chen Xin Wang Li Liu Bi-Feng Yuan Liang Cheng Beijing National Laboratory for Molecular Sciences(BNLMS) CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular Sciences Institute of ChemistryChinese Academy of SciencesBeijing 100190 School of Public Health Wuhan UniversityWuhan 430071 University of Chinese Academy of Sciences Beijing 100049

Selective methods for modulating RNA epigenetic modifications within living cells and organisms represent attractive techniques for investigating biological functions and medicinal *** contrast to enzymatic methods,abiotic chemical modulation offers access to diverse new-to-natural *** herein report a visible light-assisted bioorthogonal reaction involving flavin mononucleotide,sodium azide,and blue light *** concert with previous chemical approaches mimicking the demodification pathway,our system functions as a powerful and selective post-modification enzyme that targets N^(6)-prenyl adenosine i^(6) A in RNA and enables the efficient construction of an artificial N^(6)-cyanomethyl adenosine(cnm^(6) A).Notably,most endogenous biomacromolecular functions,including other common RNA epigenetics,remained ***,we have successfully modified i^(6) A in tRNA to cnm^(6) A in human cells and establish this system as a bona fide bioorthogonal reaction with potential applications in chemical biology and in-cell modulation.

关键词： chemical post-modification bioorthogonal reactions RNA modifications N^(6)-isopentenyl adenosine N^(6)-cyanomethyl adenosine

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A chemical labeling of N^(6)-formyl adenosine(f^(6)A) RNA

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Chinese Chemical Letters 2022年第3期33卷 1563-1566页

作者： Li-Jun Xie Cui-Lian Lin Li Liu Liang Cheng Beijing National Laboratory for Molecular Sciences(BNLMS) CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular SciencesInstitute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China

N^(6)-methyl adenosine (m^(6)A) is an eminent epigenetic mark in mRNAs that affects a broad range of biological functions in diverse species. However, the chemically inert methyl group prevents a direct labeling of this modification for subsequent detection and sequencing. Therefore, most current approaches for the labeling of m^(6)A still have limitations of relying on the utilization of corresponding methyltransferases, which resulted in the lacking of efficiency. Here we present an approach which selectively alkylated the N^(6)-formyl adenosine (f^(6)A), the key intermediate during chemical oxidation of m^(6)A, with an alkyne functionality that can be further labeled with click reactions. This covalent labeling approach will be able to facilitate in the affinity purification, detection and genome-wide profiling studies.

关键词： RNA epigenetics Chemical modulation Labeling Nucleic acids Alkylation

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