5-Jod-2'-desoxy-cytidin-5'-phosphat | 2498-43-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5-Jod-2'-desoxy-cytidin-5'-phosphat
• 英文别名: 5-iodo-2'-deoxycytidine 5'-monophosphate；5-iodo-2'-deoxy-[5']cytidylic acid；2'-Deoxy-5-iodo-5'-cytidylic acid；[(2R,3S,5R)-5-(4-amino-5-iodo-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 2498-43-3
• 化学式: C₉H₁₃IN₃O₇P
• 分子量: 433.096
• InChiKey: JYCZFDPCUJKMMG-RRKCRQDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Jod-2'-desoxy-cytidin-5'-phosphat 在 ammonium acetate 、 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 caesium carbonate 、 溶剂黄146 、 苯胺 作用下， 以 水 、 乙腈 为溶剂， 反应 25.0h， 生成 ((2R,3S,5R)-5-(4-amino-5-(5-((2-(2,4-dinitrophenyl)hydrazineylidene)methyl)thiophen-2-yl)-2-oxopyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
  参考文献：
  名称：

  dra修饰的核苷酸的合成及其在DNA上的聚合酶掺入以用于氧化还原标记

  摘要：

  5-（5-甲酰噻吩-2-基）胞嘧啶，7-（5-甲酰噻吩-2-基）-7-脱氮杂腺苷2'-脱氧核糖核苷及其5'- O将三磷酸酯（dNTP）转化为2,4-二硝基苯hydr或硝基苯并呋喃基。polymer修饰的dNTPs通过聚合酶催化的引物延伸（PEX）酶促地掺入了DNA中。direct连接的dNTPs的这种直接掺入与醛修饰的dNTPs先前报道的掺入，DNA上合成后posts的掺和进行了比较，表明直接掺入可用于掺入更多的units单元，但是，更清洁的PEX产品是通过醛的掺入并随后与肼反应。对硝基芳基aryl连接的核苷和DNA的电化学行为进行了广泛的研究，证实了,、硝基芳基和苯并呋喃氮烷基团在DNA的氧化还原标记中的潜在用途。

  DOI：

  10.1002/cplu.201200056
• 作为产物：
  描述：

  2'-脱氧胞苷-5'-单磷酸 在 碘酸 作用下， 生成 5-Jod-2'-desoxy-cytidin-5'-phosphat
  参考文献：
  名称：

  新型核苷5'-三磷酸和含炔或氨基的亚磷酰胺的合成，用于核酸的后合成功能

  摘要：

  设计并合成了一系列新的含有炔或氨基的核苷5'-三磷酸和亚磷酰胺，用于核酸的后合成功能。为此，使用了新的3-氨基丙氧基丙炔基连接基团。它包含两种替代功能：用于氨基-炔基修饰的寡核苷酸与相应的活化酯反应的氨基和用于铜（I）催化的叠氮化物-炔烃环加成（CuAAC）反应的炔基。结果表明，可以使用多种连接新接头的方法来合成各种修饰的嘧啶核苷。

  DOI：

  10.1080/15257770.2011.595379

文献信息

• Alkylsulfanylphenyl Derivatives of Cytosine and 7-Deazaadenine Nucleosides, Nucleotides and Nucleoside Triphosphates: Synthesis, Polymerase Incorporation to DNA and Electrochemical Study
  作者：Hana Macíčková-Cahová、Radek Pohl、Petra Horáková、Luděk Havran、Jan Špaček、Miroslav Fojta、Michal Hocek

  DOI：10.1002/chem.201003496

  日期：2011.5.16

  halogenated nucleosides, nucleotides and nucleoside triphosphates derived from 5‐iodocytosine and 7‐iodo‐7‐deazaadenine with methyl‐, benzyl‐ and tritylsufanylphenylboronic acids gave the corresponding alkylsulfanylphenyl derivatives of nucleosides and nucleotides. The modified nucleoside triphosphates were incorporated into DNA by primer extension by using Vent(exo‐) polymerase. The electrochemical behaviour

  来自5-碘代胞嘧啶和7-碘代-7-脱氮杂腺嘌呤的卤代核苷，核苷酸和三磷酸核苷的Suzuki-Miyaura水溶液与甲基，苄基和三苯甲基磺酰基苯基硼酸的交叉偶联反应得到了相应的核苷和核苷酸烷基硫烷基苯基衍生物。使用Vent（exo-）聚合酶通过引物延伸将修饰的三磷酸核苷掺入DNA中。烷基硫烷基苯基核苷的电化学行为表明在电极上形成致密层。修饰的核苷酸和结合了苄基或三苯硫基硫烷基苯基的DNA在[Co（NH 3）6 ] 3+中产生信号铵缓冲液，归因于Brdička催化反应，具体取决于所施加的负电位。在这种介质中反复进行恒流计时电位扫描，发现其Brdička催化反应增强，这表明在该条件下，烷基硫烷基衍生物脱保护为游离硫醇。
• Complexes of RNA and cationic peptides for transfection and for immunostimulation
  申请人：CureVac GmbH

  公开号：EP2484770A1

  公开（公告）日：2012-08-08

  The present invention relates to a complexed RNA, comprising at least one RNA complexed with one or more oligopeptides, wherein the oligopeptide has a length of 8 to 15 amino acids and has the empirical formula (Arg)l;(;Lys)m;(His)n;(Orn)o;(Xaa)x with the majority of the residues being selected from Arg, Lys, His, Orn. The invention further relates to a method for transfecting a cell or an organism, thereby applying the inventive complexed RNA. Additionally, pharmaceutical compositions and kits comprising the inventive complexed RNA, as well as the use of the inventive complexed RNA for transfecting a cell, tissue or an organism and/or for modulating, preferably inducing or enhancing, an immune response are disclosed herein.

  本发明涉及一种复合 RNA，包括至少一种与一种或多种寡肽复合的 RNA，其中寡肽的长度为 8 至 15 个氨基酸，具有经验式 (Arg)l;(;Lys)m;(His)n;(Orn)o;(Xaa)x，大部分残基选自 Arg、Lys、His、Orn。本发明进一步涉及一种转染细胞或生物体的方法，从而应用本发明的复合 RNA。此外，本文还公开了包含本发明络合 RNA 的药物组合物和试剂盒，以及本发明络合 RNA 用于转染细胞、组织或生物体和/或调节、优选诱导或增强免疫反应的用途。
• COMPLEXES OF RNA AND CATIONIC PEPTIDES FOR TRANSFECTION AND FOR IMMUNOSTIMULATION
  申请人：Curevac GmbH

  公开号：EP2188379A1

  公开（公告）日：2010-05-26
• COMPLEXES OF RNA AND CATIONIC PEPTIDES FOR TRANSFECTION AND FOR IMMUNOSTIMULATION
  申请人：CureVac AG

  公开号：US20160184406A1

  公开（公告）日：2016-06-30

  The present invention relates to a complexed RNA, comprising at least one RNA complexed with one or more oligopeptides, wherein the oligopeptide, which has the function of cell-penetrating peptide (CPP), has a length of 8 to 15 amino acids and has the empirical formula (Arg) l ; (Lys) m ; (His) n ; (Om) o ; (Xaa) x with the majority of residues being selected from Arg, Lys, His, Om. The invention further relates to a method for transfecting a cell or an organism, thereby applying the inventive complexed RNA. Additionally, pharmaceutical compositions and kits comprising the inventive complexed RNA, as well as the use of the inventive complexed RNA for transfecting a cell, tissue or an organism and/or for modulating, preferably inducing or enhancing, an immune response are disclosed herein.
• METHODS OF TREATING PHENYLKETONURIA WITH MRNA ENCODING PHENYLALANINE HYDROXYLASE (PAH)
  申请人：CureVac AG

  公开号：US20190167808A1

  公开（公告）日：2019-06-06

  The present invention relates to a complexed RNA, comprising at least one RNA complexed with one or more oligopeptides, wherein the oligopeptide has a length of 8 to 15 amino acids and has the empirical formula (Arg) l ;(;Lys) m ;(His) n ;(Orn) o ;(Xaa) x . The invention further relates to a method for transfecting a cell or an organism, thereby applying the inventive complexed RNA. Additionally, pharmaceutical compositions and kits comprising the inventive complexed RNA, as well as the use of the inventive complexed RNA for transfecting a cell, tissue or an organism and/or for modulating, preferably inducing or enhancing, an immune response are disclosed herein.