2'-deoxy-2'-(2-nitrophenyldithio)cytidine | 603112-54-5

• 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'-deoxy-2'-(2-nitrophenyldithio)cytidine
• 英文别名: 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-[(2-nitrophenyl)disulfanyl]oxolan-2-yl]pyrimidin-2-one
• CAS: 603112-54-5
• 化学式: C₁₅H₁₆N₄O₆S₂
• 分子量: 412.447
• InChiKey: HZTVAUDKBAZMMR-ICGCDAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  205
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-deoxy-2'-(2-nitrophenyldithio)cytidine 在 吡啶 、 三氯硫磷 、 Proton Sponge 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 4.45h， 生成 2'-deoxy-2'-(tert-butyldithio)cytidine-α-thiotriphosphate
  参考文献：
  名称：

  2‘-Mercaptonucleotide Interference Reveals Regions of Close Packing within Folded RNA Molecules

  摘要：

  The 2'-hydroxyl group makes essential contributions to RNA structure and function. As an approach to assess the ability of a mercapto group to serve as a functional analogue for the 2'-hydroxyl group, we synthesized 2'-mercaptonucleotides for use in nucleotide analogue interference mapping. To correlate the observed interference effects with tertiary structure, we used the independently folding DeltaC209 P4-P6 domain from the Tetrahymena group I intron. We generated populations of DeltaC209 P4-P6 molecules containing 2'-mercaptonucleotides located randomly throughout the domain and separated the folded molecules from the unfolded molecules by nondenaturing gel electrophoresis. Iodine-induced cleavage of the RNA molecules revealed the sites at which 2'-mercaptonucleotides interfere with folding. These interferences cluster in the most densely packed regions of the tertiary structure, occurring only at sites that lack the space and flexibility to accommodate a sulfur atom. Interference mapping with 2'-mercaptonucleotides therefore provides a method by which to identify structurally rigid and densely packed regions within folded RNA molecules.

  DOI：

  10.1021/ja035175y
• 作为产物：
  描述：

  2-硝基苯硫氯 、 2'-deoxy-2'-(2-(trimethylsilyl)ethyl)thiocytidine 以 甲醇 为溶剂， 反应 4.0h， 以42%的产率得到2'-deoxy-2'-(2-nitrophenyldithio)cytidine
  参考文献：
  名称：

  由2-（三甲基甲硅烷基）乙基硫化物直接制备核苷乙烯基二硫化物，获得乙烯基硫醇。

  摘要：

  我们在这里报告了使用2-乙烯基三（三甲基甲硅烷基）乙基（TMSE）硫化物与亚磺酰氯的新反应，在温和条件下以高收率直接制备各种核苷乙烯基二硫化物的方法。该反应允许从稳定的甲硅烷基硫化物制备各种混合的二硫化物，而不会形成可氧化的和/或不稳定的硫醇。通过该反应易于制备乙烯基二硫化物，将为乙烯基硫醇化学提供新的见解。

  DOI：

  10.1021/ol071088p

文献信息

• PROCESS FOR PREPARING DISULPHIDES AND THIOSULPHINATES AND COMPOUNDS PREPARED
  申请人：Decout Jean-Luc

  公开号：US20090264637A1

  公开（公告）日：2009-10-22

  Process for preparing a compound of the formula (I) R1-S(O) x —S(O) y R2 in which R1 represents a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen; R2, independently of R1, represents a carbon-containing group or a molecular hydrocarbon radical which can be substituted and/or interrupted by one or more atoms and/or by one or more groups containing one or more atoms, said atoms being selected from N, O, P, S, Si and X, where X represents a halogen, and x and y are selected from 0 and 1 in such a way that the sum of x and y is not more than 1, characterized in that a compound of formula (II) R1-S(O) x —R3-Si(R4)(R5)(R6) in which R3 represents a hydrocarbon chain of two carbon atoms, which is optionally unsaturated and/or substituted, and R4, R5 and R6, which are identical or different, each represent, independently of one another, a hydrocarbon group, is reacted with a compound of formula (VII) R2-S(O) y —X in which X represents a halogen, intermediate compounds, and compounds prepared.

  制备化合物的过程（I）R1-S(O)x—S(O)yR2的公式，其中R1代表一个可以被一个或多个原子和/或一个或多个含有一个或多个原子的基团取代和/或中断的分子烃基团，所述原子选自N、O、P、S、Si和X，其中X代表一个卤素；独立于R1，R2代表一个含碳基团或一个可以被一个或多个原子和/或一个或多个含有一个或多个原子的基团取代和/或中断的分子烃基团，所述原子选自N、O、P、S、Si和X，其中X代表一个卤素，x和y选自0和1，使得x和y的和不超过1，其特征在于将公式（II）R1-S(O)x—R3-Si(R4)(R5)(R6)中R3代表一个含有两个碳原子的烃链，可以是不饱和和/或取代的，R4、R5和R6，它们相同或不同，每个独立地代表一个烃基团，与公式（VII）R2-S(O)y—X中的X代表一个卤素的化合物反应，中间化合物和制备的化合物。
• US8236945B2
  申请人：——

  公开号：US8236945B2

  公开（公告）日：2012-08-07
• Direct Preparation of Nucleoside Vinyl Disulfides from 2-(Trimethylsilyl)ethyl Sulfides, an Access to Vinylthiols
  作者：Béatrice Gerland、Jérôme Désiré、Michel Lepoivre、Jean-Luc Décout

  DOI：10.1021/ol071088p

  日期：2007.8.1

  preparation of various nucleoside vinyl disulfides in high yields under mild conditions using the new reaction of vinyl 2-(trimethylsilyl)ethyl (TMSE) sulfides with sulfenyl chlorides. This reaction allows the preparation of various mixed disulfides from stable silyl sulfides without formation of oxidizable and/or unstable thiols. The easy preparation of vinyl disulfides through this reaction should offer

  我们在这里报告了使用2-乙烯基三（三甲基甲硅烷基）乙基（TMSE）硫化物与亚磺酰氯的新反应，在温和条件下以高收率直接制备各种核苷乙烯基二硫化物的方法。该反应允许从稳定的甲硅烷基硫化物制备各种混合的二硫化物，而不会形成可氧化的和/或不稳定的硫醇。通过该反应易于制备乙烯基二硫化物，将为乙烯基硫醇化学提供新的见解。
• 2‘-Mercaptonucleotide Interference Reveals Regions of Close Packing within Folded RNA Molecules
  作者：Jason P. Schwans、Cecilia N. Cortez、Joe M. Olvera、Joseph A. Piccirilli

  DOI：10.1021/ja035175y

  日期：2003.8.1

  The 2'-hydroxyl group makes essential contributions to RNA structure and function. As an approach to assess the ability of a mercapto group to serve as a functional analogue for the 2'-hydroxyl group, we synthesized 2'-mercaptonucleotides for use in nucleotide analogue interference mapping. To correlate the observed interference effects with tertiary structure, we used the independently folding DeltaC209 P4-P6 domain from the Tetrahymena group I intron. We generated populations of DeltaC209 P4-P6 molecules containing 2'-mercaptonucleotides located randomly throughout the domain and separated the folded molecules from the unfolded molecules by nondenaturing gel electrophoresis. Iodine-induced cleavage of the RNA molecules revealed the sites at which 2'-mercaptonucleotides interfere with folding. These interferences cluster in the most densely packed regions of the tertiary structure, occurring only at sites that lack the space and flexibility to accommodate a sulfur atom. Interference mapping with 2'-mercaptonucleotides therefore provides a method by which to identify structurally rigid and densely packed regions within folded RNA molecules.