CAS: 13957-31-8; 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)-4-Thioxo-3,4-Dihydropyrimidin-2(1H)-One

该化合物是经过修改的核素,在RNA生物学中起着重要作用,其特点是,在氨基质基质的4个位置上存在硫磺原子,使其与标准的氨基质有区别.这种修改可以影响RNA分子的稳定性和功能,影响翻译和RNA折叠等过程.4-硫氨已知参与各种生物化学途径,并经常研究其在分子生物学和治疗环境中的潜在应用.该化合物溶于核素典型的水和外表特性,包括形成氢联结和参与基配对的能力.其独特的结构使其能够与特定的酶和蛋白质互动,使其成为以RNA动态和功能为重点的研究的宝贵工具.此外,4-硫氨在笔录过程中可以纳入RNA,这可能会改变产生的RNA线的特性,使人们深入了解经修改的核素在细胞过程中的作用.

结构式图片

相似化合物

5580-20-1 3690-10-6 58-96-8

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CAS号55003-25-3 (2R,3R,4R,5R)-2... | CAS号109389-25-5 2(1H)-Pyrimidin... | CAS号58-96-8 尿苷 | CAS号15049-50-0 Uridine,4-thio-... | CAS号1748-04-5 2,3,5-三苯甲酰尿苷 | CAS号4105-38-8 2,3,5-三乙酰尿苷 | CAS号136055-16-8 1-((2R,3R,4R,5R... | CAS号10457-16-6 2',3',5,-tris-O... | CAS号58-96-8 尿苷

合成工艺路线路线简述

    📜尿嘧啶核苷置于吡啶,Ammonium Hydroxide,Tetraphosphorus Decasulfide,碘体系中,用 水 用作溶剂,化学反应 6.75H,反应生成4-硫代尿苷
    参考文献:细菌trna中4-甲基硫尿苷的合成及代谢命运.
    标题:细菌trna中4-甲基硫尿苷的合成及代谢命运.
    摘要:通过合成和分析化学的结合,在细菌trna中证实了修饰的核苷4-甲基硫尿苷的结构.修饰的丰度低,在甲基化剂诱导细菌胁迫后形成.这证明了其作为天然trna病变的性质.通过脉冲追踪分析,我们通过体内的脱硫甲基化机制显示了其修复作用.
    Doi:10.1002/cbic.202000272

    海关参考信息

    专利信息


    专利号:US-9884885-B2
    优先权日:2009-05-18
    标题:Synthesis of labile base protected-modified deoxy and modified ribo nucleosides, corresponding phosphoramidites and supports and their use in high purity oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to novel method of synthesis of RNA utilizing N-2-acetyl protected guanine as nucleoside base, nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-acetyl protected guanine as nucleoside base protecting group, which is significantly faster base labile protecting group, yet significantly more stable than commonly utilized-2-isobutyryl guanosine is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups, including acetyl group from guanine and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of acetyl protecting groups of the natural deoxy and ribonucleosides occurs under substantially reduced time in contact with mild deprotection conditions such as mild bases, secondary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is designed to lead to high purity large scale therapeutic grade oligonucleotide chimeras which consist of fluoro sugar modification in conjunction with deoxy nucleosides, ribonucleosides, modified base and modified sugar nucleosides. This approach is further designed to use acetyl guanine protecting group when other bases are sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides.

    专利号:US-8981076-B2
    优先权日:2008-11-29
    标 题 :Synthesis of N-FMOC protected deoxy nucleosides, ribo nucleosides, modified deoxy and ribo nucleosides, and phosphoramidites, and their use in oligonucleotide synthesis
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P; CHEMGENES CORP
    摘要:This invention relates to synthesis of novel -N-FMOC protected nucleosides, succinates, phosphoramidites, corresponding solid supports that are suitable for oligo deoxy nucleosides and RNA oligonucleotide synthesis. Our discovery using N-FMOC as nucleoside base protecting group, which is highly base labile protecting group is a novel approach to obtain highest purity oligonucleotides. This approach is designed to lead to very high purity and very clean oligonucleotide, after efficient removal of the protecting groups and to produce high purity therapeutic grade DNA oligonucleotides, RNA oligonucleotides, diagnostic DNA, diagnostic RNA for microarray platform. The deprotection of FMOC protecting groups of the natural deoxy and ribonucleosides occurs under very mild deprotection conditions such as mild bases, secondary and tertiary amines for removal of such groups under such conditions would allows synthesis of various DNA and RNA of highest purity for diagnostics and therapeutic application. This approach is further designed to use FMOC protecting group on various base sensitive nucleoside, and for use in oligo peptide synthesis and for support bound oligo nucleotides. DNA oligonucleotides containing 3′-end dA at the 3′-terminal will be produced using the FMOC-dA-supports would lead to much reduced M−1 deletion sequences, and thereby high purity.

    专利号:US-10167308-B2
    优先权日:2013-09-14
    标题:Highly efficient synthesis of long RNA using reverse direction approach
    发明人:SRIVASTAVA SURESH C; SRIVASTAVA NAVEEN P
    权利人:CHEMGENES CORP
    摘要:The present invention relates to novel process of reverse 5′→3′ directed synthesis of RNA oligomers in the range of about 100-mer to about 200-mer has been developed and disclosed. Using that method demonstrated high quality RNA synthesis with coupling efficiency approaching 99%.

    专利号:US-2005130201-A1
    优先权日:2003-10-14
    标 题 :Splint-assisted enzymatic synthesis of polyribounucleotides
    发明人:DERAS MICHAEL; PLEISS JEFFREY A; SCARINGE STEPHEN
    权利人:DHARMACON INC
    摘要:The present invention comprises methods and compositions for splint-assisted enzymatic synthesis of polyribonucleotides using an RNA polymerizing enzyme. The invention provides ligating ribonucleotides comprising ligating a donor RNA molecule to an acceptor RNA molecule in the presence of RNA ligase and a splint, wherein the donor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety, the acceptor RNA molecule is comprised of at least one nucleotide and a ligation linker moiety and the splint is comprised of a polyribonucleotide. The invention also provides splints for use in splint-assisted enzymatic synthesis using an RNA polymerizing enzyme.

    专利号:US-2003049619-A1
    优先权日:2001-03-21
    标题 :Methods for the synthesis of polynucleotides and combinatorial libraries of polynucleotides
    发明人:DELAGRAVE SIMON; MARRS BARRY
    摘要:Methods for the synthesis of polynucleotides and derivatives thereof are provided. Methods for the preparation of combinatorial libraries of polynucleotides are also provided. In addition, methods for the preparation and identification of polynucleotides having a predetermined property are provided.

    专利号:US-11407993-B2
    优先权日:2017-02-14
    标 题 :Method for the synthesis of DNA conjugates by micellar catalysis
    发明人:BHAT AVINASH SHASHIDHAR; KLIKA SKOPIC MATEJA; BRUNSCHWEIGER ANDREAS; WEBERSKIRCH RALF
    权利人:UNIV DORTMUND TECH
    摘要:A method for the synthesis of a chimeric conjugate molecule by micellar catalysis that may form part of DNA-encoded compound libraries. A DNA-coupled organic starter molecule may be reacted with another organic compound, using a catalyst located within a micelle, to form a conjugate of an organic candidate compound coupled to a DNA identifier tag.

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    ✅ COA系统入驻 | 共享模式

    主要参考文献

    1. Burger, K., Mühl, B., Kellner, M., et al. 4-Thiouridine inhibits rRNA synthesis and causes a nucleolar stress response. RNA Biol. 10(10), 1623-1630 (2013). 2. Thomas, G., and Favre, A. 4-Thiouridine triggers both growth delay induced by near-ultraviolet light and photoprotection. European Journal of Biochemistry 113(1), 67-74 (1980). 3. Harris, M.E., and Christian, E.L. RNA crosslinking methods. Methods in Enzymology 468, 127-146 (2009).

    合成参考文献


    摘要:M. N. Lipsett, J. Biol. Chem. 240, 3975 (1965).
    参考文献:10.1016/s1011-1344(02)00272-5
    摘要:Oppezzo OJ, Pizarro RA. Transient reduction in the tRNA 4-thiouridine content induced by ultraviolet A during post-irradiation growth in Enterobacter cloacae. Journal of Photochemistry and Photobiology B: Biology. 2002 Apr;66(3):207–12. doi: 10.1016/s1011-1344(02)00272-5.
    参考文献:10.1134/s1068162008010123
    摘要:Bulygin KN, Baouz-Drahy S, Favre A, Ven'iaminova AG, Graíífer DM, Karpova GG. [The environment of tRNA 3'-terminus in 80S ribosome A and P sites]. Bioorg Khim. 2008 Jan;34(1):96–106. doi: 10.1134/s1068162008010123.
    参考文献:10.1007/978-1-59745-033-1_9
    摘要:Zeiner GM, Cleary MD, Fouts AE, Meiring CD, Mocarski ES, Boothroyd JC. RNA analysis by biosynthetic tagging using 4-thiouracil and uracil phosphoribosyltransferase. Methods Mol Biol. 2008;419():135–46. doi: 10.1007/978-1-59745-033-1_9.
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