CAS: 26929-65-7; 1-((2R,3R,4S,5R)-3-Azido-4-Hydroxy-5-(Hydroxymethyl)Tetrahydrofuran-2-yl)Pyrimidine-2,4(1H,3H)-Dione

该化合物是一种经过修改的核核素派衍生物,在3号位置上有一个Azido功能组,在氧化醇环(四氢呋喃)上有一个氢氧甲基替代体.该化合物对合成化学和生化研究很感兴趣,因为它具有作为点击化学应用的多功能中间体的潜力,能够通过azide-alkyne循环化与 alkynes有选择地结合.氢氧基集团的存在会增加其在极地溶剂中的溶性,有助于进一步的衍生.其结构特征使其适合用于核肺酸相互作用,或设计具有治疗或诊断性定制特性的经修改的寡核素.在复杂的生物系统中也可进行生物博质标签.

结构式图片

上下游产品

CAS号3736-77-4 2,2'-脱水尿苷 | CAS号58-96-8 尿苷 | CAS号66-22-8 尿嘧啶 | CAS号26889-39-4 2'-氨基脱氧尿苷 | CAS号174221-86-4 2′-Amino-5′-O-[... | CAS号51034-68-5 2'-叠氮基胞苷

合成工艺路线路线简述

    尿嘧啶核苷置于碳酸二苯酯,四甲基乙二胺,叠氮基三甲基硅烷,Lithium Fluoride体系中,用 N,N-二甲基甲酰胺 用作溶剂,化学反应生成2'-叠氮-2'-脱氧尿苷
    参考文献:通过呋喃修饰的寡脱氧核苷酸的原位氧化实现前所未有的 C 选择性链间交联
    标题:通过呋喃修饰的寡脱氧核苷酸的原位氧化实现前所未有的 C 选择性链间交联
    摘要:形成链间交联的化学试剂已在癌症治疗中使用了很长时间.它们共价连接两条 Dna 链,从而阻止转录.然而,交联修复酶可以恢复转录过程,导致对某些抗癌药物的耐药性.这些交联修复过程的机制尚未完全揭示.本研究的障碍之一是缺乏足够数量的明确,稳定,交联的双链体来研究交联修复酶的途径.我们的小组开发了一种交联策略,其中呋喃部分被整合到寡脱氧核苷酸 (Odn) 中.这些呋喃修饰的核酸可以在用 N-溴代琥珀酰亚胺选择性呋喃氧化后形成链间交联.我们在此报告了通过酰氨基或脲基接头在尿苷的 2'-位掺入呋喃部分.所得修饰的 Odn 显示出前所未有的选择性,可向与修饰残基相对的胞苷交联,形成一个特定的交联双链体,可以高产率分离.此外,形成的交联双链体的结构可以明确表征.
    Doi:10.1021/ja1048169

    海关参考信息

    专利信息


    专利号:US-5118802-A
    优先权日:1983-12-20
    标 题:DNA-reporter conjugates linked via the 2' or 5'-primary amino group of the 5'-terminal nucleoside
    发明人:SMITH LLOYD M; FUNG STEVEN; KAISER JR ROBERT J
    权利人:CALIFORNIA INST OF TECHN
    摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

    专利号:US-2007065922-A1
    优先权日:2005-09-21
    标题 :Biocatalytic synthesis of aminodeoxy purine N9-beta-D-nucleosides containing 3-amino-3-deoxy-beta-D-ribofuranose, 3-amino-2,3-dideoxy-beta-D-ribofuranose, and 2-amino-2-deoxy-beta-D-ribofuranose as sugar moieties
    发明人:BARAI VLADIMIR N; EROSHEVSKAYA LUDMILLA A; MIKHAILOPULO IGOR A; AZHAYEV ALEX V; LAPINJOKI SEPPO P
    权利人:METKINEN OY
    摘要:Purine N 9 -β-D-nucleosides containing 3-amino-3-deoxy-β-D-ribofaranose, 3-amino-2,3-dideoxy-β-D-ribofuranose, and 2-amino-2-deoxy-β-D-ribofuranose as sugar moieties are synthesized by biocatalytic transglycosylation of purine bases and the respective 3′-amino-3′-deoxyuridine, 3′-amino-3′-deoxythymidine and 2′-amino-2′-deoxyuridine as donors of the carbohydrate moiety, and the cells of Escherichia coli as a biocatalyst or glutaraldehyde (GA) treated cells of Escherichia coli as a biocatalyst or a mixture of thymidine (uridine) phosphorylase and purine nucleoside phosphorylase.

    专利号:US-5116741-A
    优先权日:1988-04-12
    标题 :Biosynthetic uses of thermostable proteases
    发明人:BRYAN PHILIP N; PANTOLIANO MICHAEL W; ROLLENCE MICHELE L; WONG CHI H
    权利人:GENEX CORP
    摘要:The invention relates to the novel use of mutants of subtilisin in organic syntheses reactions in non-native environments. Especially the invention relates to methods for the use of mutant subtilisins in organic solvents for the catalysis of reactions involving ester formation and cleavage, including acylations and deacylations, and amidations and deamidations. The methods provide novel strategies which are useful in the synthesis of deoxynucleosides, dideoxynucleosides, peptides, sugars and the like.

    专利号:US-5118800-A
    优先权日:1983-12-20
    标 题 :Oligonucleotides possessing a primary amino group in the terminal nucleotide
    发明人:SMITH LLOYD M; FUNG STEVEN; KAISER JR ROBERT J
    权利人:CALIFORNIA INST OF TECHN
    摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieties may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

    专利号:US-5015733-A
    优先权日:1983-12-20
    标题 :Nucleosides possessing blocked aliphatic amino groups
    发明人:SMITH LLOYD M; FUND STEVEN; KAISER JR ROBERT J
    权利人:CALIFORNIA INST OF TECHN
    摘要:The invention consists of compounds and methods for the synthesis of oligonucleotides which contain one or more free aliphatic amino groups attached to the sugar moieties of the nucleoside subunits. The synthetic method is versatile and general, permitting amino groups to be selectively placed at any position on oligonucleotides of any composition or length which is attainable by current DNA synthetic methods. Fluorescent dyes or other detectable moieites may be covalently attached to the amino groups to yield the corresponding modified oligonucleotide.

    专利号:US-11939363-B2
    优先权日:2017-02-28
    标题:Translatable molecules and synthesis thereof
    发明人:LIMPHONG PATTRARANEE; TACHIKAWA KIYOSHI; CHIVUKULA PADMANABH; MATSUDA DAIKI; CALE ARISA
    权利人:ARCTURUS THERAPEUTICS INC
    摘要:A range of therapeutic mRNA molecules expressible to provide a target polypeptide or protein. The RNA molecules can contain one or more 5-methoxyuridines and 5-methylcytidines. Further provided are DNA templates, which can be transcribed to provide a target mRNA, and can have altered nucleotides, such as reduced deoxyadenosines. Also provided are processes for making the therapeutic mRNA molecules. The RNA molecules can be translated in vitro or in vivo to provide an active polypeptide or protein. The RNA molecules can be included in a composition used for preventing, treating, or ameliorating at least one symptom of a disease or condition in a subject in need thereof.
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    合成参考文献


    参考文献:10.1021/jp101367s
    摘要:Gai XS, Fenlon EE, Brewer SH. A sensitive multispectroscopic probe for nucleic acids. J Phys Chem B. 2010 Jun 17;114(23):7958–66. doi: 10.1021/jp101367s.
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