2’-deoxycytidine-5’-O-monophosphorothioate | 64145-27-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2’-deoxycytidine-5’-O-monophosphorothioate
• 英文别名: 5’-dCMPS；2'-Desoxycytidin-5'-O-phophorothioat；P-thio-2'-deoxy-[5']cytidylic acid；[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-sulfanylphosphinic acid
• CAS: 64145-27-3
• 化学式: C₉H₁₄N₃O₆PS
• 分子量: 323.266
• InChiKey: FHBXKBNKQMSUIJ-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 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：
  170
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  硫酸二甲酯 、 2’-deoxycytidine-5’-O-monophosphorothioate 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Cummins, Jane H.; Potter, Barry V. L., Phosphorus and Sulfur and the Related Elements, 1987, vol. 30, p. 589 - 592

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2’-deoxycytidine-5’-O-monophosphorothioate
  参考文献：
  名称：

  用于脱氧核糖核苷，DNA寡核苷酸及其热解类似物磷酸化的有效试剂。

  摘要：

  [反应：见正文]从2巯基乙酸甲酯分三步制备亚磷酰胺11，并证明了2'-脱氧核糖核苷的常规5'-/ 3'-磷酸酯/硫代磷酸酯单酯衍生物和DNA寡核苷酸的合成效率。而且，使用11使得能够以高收率（＞ 95％）制备二核苷硫代磷酸酯类似物26，而热解硫代磷酸酯保护基团的裂解最小（＜2％）。

  DOI：

  10.1021/ol0516263

文献信息

• NOVEL ANTI-HIV DRUG
  申请人：KAJI, Akira

  公开号：EP0724882A1

  公开（公告）日：1996-08-07

  An anti-HIV agent which comprises as an active ingredient one or more species selected from phosphodiester bonding type or phosphorothioester bonding type oligoribonucleotides with 2-8 bases represented by the 4 bases of the below formulae (III), (VII), (XI), (XVII) and (XXI)    GpGpGpGp   (III)    pGpGpGpG   (VII)    GsGsGsGp   (XI)    pGsGsGsG   (XVII)    GsGsGsG   (XXI) wherein G represents guanosine structure, p is a phosphoric acid residue which forms an ester bonding with neighboring G, and s is the thiophosphoric acid residue which forms the phosphorothioester bonding with neighboring G.

  一种抗艾滋病毒制剂，其活性成分包括一种或多种选自磷酸二酯键型或硫代磷酸酯 键型的寡核苷酸，这些寡核苷酸的 2 至 8 个碱基由下式(III)、(VII)、(XI)、(XVII) 和(XXI)中的 4 个碱基代表 GpGpGpGp (III) pGpGpGpG (VII) GsGsGsGp (XI) pGsGsGsG (XVII) GsGsGsG (XXI) 其中 G 代表鸟苷结构，p 是磷酸残基，与邻近的 G 形成酯键，s 是硫代磷酸残基，与邻近的 G 形成硫代磷酸酯键。
• NOVEL ANTI-HIV AGENT
  申请人：KAJI, Akira

  公开号：EP0743318A1

  公开（公告）日：1996-11-20

  An anti-HIV agent which comprises as an active ingredient one or more selected from phosphorothioate bonding type or phosphodiester bonding type oligodeoxynucleotides having 2 to 8 bases of the below formulae (I), (II), (III), (IV) and (V):         (Gs)nG     (I)         (Gs)nGp     (II)         p(Gs)nG     (III)         pGs(Gs)nGp     (IV)         pGpGpGpGp     (V) wherein G represents deoxyguanosine structure, p is a phosphoric acid residue which forms an ester bonding with the adjacent G, s is the phosphorothiophosphoric acid residue which forms a phosphorothioester bonding with the adjacent G, and n is an integer of from 2 to 7.

  一种抗艾滋病毒制剂，其活性成分包括一种或多种选自硫代磷酸键合型或磷酸二酯键合型的寡聚脱氧核苷酸，这些寡聚脱氧核苷酸具有 2 至 8 个碱基，如下式(I)、(II)、(III)、(IV)和(V)所示： (Gs)nG (I) (Gs)nGp (II) p(Gs)nG (III) pGs(Gs)nGp (IV) pGpGpGpGp (V) 其中 G 代表脱氧鸟苷结构，p 是与相邻 G 形成酯键的磷酸残基，s 是与相邻 G 形成硫代磷酸键的硫代磷酸残基，n 是 2 到 7 的整数。
• Methods for modulating taste receptors
  申请人：MARS, INCORPORATED

  公开号：US11185100B2

  公开（公告）日：2021-11-30

  Amino acids present in domains of an umami taste receptor are described herein, wherein the amino acids interact with at least one nucleotide derivative and/or at least one transmembrane compound that potentiates, modulates, increases, and/or enhances the activity of the umami receptor. Such compounds can be used in flavor compositions to enhance the umami taste and/or palatability of food products.

  本文描述了存在于鲜味受体结构域中的氨基酸，其中氨基酸与至少一种核苷酸衍生物和/或至少一种跨膜化合物相互作用，从而增强、调节、增加和/或提高鲜味受体的活性。此类化合物可用于调味组合物，以增强食品的鲜味和/或适口性。
• Post-synthesis labeling of nucleic acids, assays using nucleic acids that are labeled post-synthetically, single nucleotide polymorphism detection, and associated compounds and microarrays
  申请人：MOTOROLA, INC.

  公开号：US20030119005A1

  公开（公告）日：2003-06-26

  An assay is provided for nucleic acids that can be post-synthetically labeled, wherein modified nucleoside triphosphates are used that are more efficiently and specifically incorporated during nucleic acid synthesis than labeled nucleoside triphosphates. In a preferred embodiment, nucleoside &agr;-thiotriphosphates are utilized. Maleimide or iodoacetamide conjugating moieties can be attached post-synthetically. The conjugating moieties may include a reporter group. Also disclosed are new methods for detecting single nucleotide polymorphism.

  提供了一种可在合成后标记核酸的检测方法，其中使用了修饰的核苷三磷酸酯，这种核苷三磷酸酯在核酸合成过程中比标记的核苷三磷酸酯更有效、更特异。在一个优选的实施方案中，使用的是核苷三磷酸酯。马来酰亚胺或碘乙酰胺共轭分子可在合成后连接。共轭分子可包括报告基团。还公开了检测单核苷酸多态性的新方法。
• A DFDL UV picosecond fluorescence spectrometer: Application to aqueous solutions of peptides and nucleotide dye conjugates
  作者：Ralf Schwarzwald、Claus Seidel、Roger S. Goody、Klaus P. Kühn、Karl Otto Greulich

  DOI：10.1002/bbpc.19890930324

  日期：1989.3

  AbstractUsing a new type of fluorescence lifetime spectrometer, the time resolution of single shot fluorescence detection is improved by two orders of magnitude. The spectrometer is based on a streak camera and an excimer laser pumped distributed feedback dye laser (DFDL) providing UV pulses of 50 μJ and 15 ps FWHM, corresponding to a peak power of ∼ 5 · 106 W in the ultraviolet. —This spectrometer is used to investigate the fluorescence decay of peptides containing a tyrosine as the single fluorophore. Peptides with tyrosine at the N‐terminus reveal a biexponential decay, while peptides with C‐terminal tyrosine are mainly monoexponential. This difference can be explained by the relative orientation of the fluorescing phenol ring and the quenching peptide bond. —The fluorescence decay of a number of peptides with tyrosine in a non terminal position can be described by two lifetimes, 2.3 · 0.1 ns and 380 ± 70 ps, where the percentage of the long lifetime increases to up to 100% when the rotational flexibility of the peptide chain decreases, either due to increasing weight of the chain or due to formation of an H‐bridge. —Similar processes seem to be relevant for the fluorescence of the dye coumarin 120 coupled to nucleotides. The fluorescence lifetime of such molecules is significantly different, so that the four DNA nucleotides can be identified on the basis of the fluorescence decay of the attached dye.