5-chloro-4-thiouridine | 919782-32-4

• 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: 5-chloro-4-thiouridine
• 英文别名: 5-Chloro-1-beta-D-ribofuranosyl-4-sulfanylidene-3,4-dihydropyrimidin-2(1H)-one；5-chloro-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-sulfanylidenepyrimidin-2-one
• CAS: 919782-32-4
• 化学式: C₉H₁₁ClN₂O₅S
• 分子量: 294.716
• InChiKey: AOSZAECHXRGYEG-UAKXSSHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-chloro-4-thiouridine 、 beta-胸苷 以 水 为溶剂， 生成 7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(4-hydroxy-5-hydroxy-methyl-tetrahydro-furan-2-yl)-4a-methyl-4a,9a-dihydro-1H,7H-9-thia-1,3,5,7-tetraaza-fluorene-2,4,6-trione 、 7-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-(4-hydroxy-5-hydroxy-methyl-tetrahydro-furan-2-yl)-4a-methyl-4a,9a-dihydro-1H,7H-9-thia-1,3,5,7-tetraaza-fluorene-2,4,6-trione
  参考文献：
  名称：

  Photoinduced Fluorescent Cross-Linking of 5-Chloro- and 5-Fluoro-4-thiouridines with Thymidine

  摘要：

  Two highly fluorescent, thermally stable diastereomeric photoadducts, 3a,b, are formed when either 5-chloro-4-thiouridine, 1, or 5-fluoro-4-thiouridine, 2, are photoexcited with 366 nm UV light in the presence of thymidine (T). 5-Fluoro-4-thiouridine, 2, exhibits photoreactivity much higher than that of the 5-chloro derivative 1. In both cases the photoreaction is very clean, leading to highly eficient conversion of the 5-halogeno-4-thiouridine (1, 2) and T to photoadducts 3a,b. The identity and structure of 3a was confirmed using mass spectrometry and 2-D NMR. The epimeric relationship of 3a,b was established by UV circular dichroism spectroscopy. The geometry of the fluorescent photoadduct is consistent with formation of an interstrand cross-link in a DNA duplex if 1 or 2 is flanked by T in an opposite strand.

  DOI：

  10.1021/jo902136k
• 作为产物：
  描述：

  5-chloro-2',3',5'-tri-O-acetyluridine 在 tetraphosphorus decasulfide 、 氨 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 生成 5-chloro-4-thiouridine
  参考文献：
  名称：

  5-取代-4-硫代嘧啶核苷核磁共振谱的系统归属

  摘要：

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.3980

文献信息

• Photocrosslinking probes and uses of the same
  申请人：Franzen Stefan

  公开号：US20070082349A1

  公开（公告）日：2007-04-12

  A method of detecting a target nucleic acid is disclosed, the method comprising detecting the presence of a fluorescent covalent crosslinked product from non-fluorescent precursors. The fluorescent covalent crosslinked product comprises a novel fluorophore structure. Also described are methods of synthesizing probe molecules that can form fluorescent covalent crosslinked products with nucleic acid targets and arrays comprising such probes.
• US7868161B2
  申请人：——

  公开号：US7868161B2

  公开（公告）日：2011-01-11
• [EN] PHOTOCROSSLINKING PROBES AND USES OF THE SAME<br/>[FR] SONDES DE PHOTORETICULATION ET LEURS UTILISATIONS
  申请人：NORTH CAROLINA UNIVERSITY

  公开号：WO2007014348A2

  公开（公告）日：2007-02-01

  [EN] A method of detecting a target nucleic acid is disclosed, the method comprising detecting the presence of a fluorescent covalent crosslinked product from non-fluorescent precursors. The fluorescent covalent crosslinked product comprises a novel fluorophore structure. Also described are methods of synthesizing probe molecules that can form fluorescent covalent crosslinked products with nucleic acid targets and arrays comprising such probes.
  [FR] La présente invention a trait à un procédé de détection d'un acide nucléique cible, le procédé comprenant la détection de la présence d'un produit réticulé covalent fluorescent à partir de précurseurs non fluorescents. Le produit réticulé covalent fluorescent comporte une nouvelle structure de fluorophore. L'invention a également trait à des procédés de synthèse de molécules sondes qui peuvent former des produits réticulés covalents fluorescents avec des cibles d'acide nucléique et des jeux de microéchantillons comportant de telles sondes.
• Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides
  作者：Xiaohui Zhang、Jian Wang、Yao-Zhong Xu

  DOI：10.1002/mrc.3980

  日期：2013.9

  characterization of 5‐substituted‐4‐thiopyrimidine nucleosides (ribonucleosides and 2'‐deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5‐bromo‐4‐thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4‐thiopyrimidine nucleosides are compared, and the key contributing

  使用 NMR 光谱对 5-取代-4-硫代嘧啶核苷（核糖核苷和 2'-脱氧核苷）进行明确表征。5-溴-4-硫尿苷和相关核苷的所有质子和碳信号的分配是通过 COZY 和 HMQC 技术系统地进行并牢固建立的。比较了各种 4-硫代嘧啶核苷的 NMR 数据，并讨论了关键影响因素。这里介绍的方法适用于其他修饰的核苷和核苷酸，以及核碱基。版权所有 © 2013 John Wiley & Sons, Ltd.
• Photoinduced Fluorescent Cross-Linking of 5-Chloro- and 5-Fluoro-4-thiouridines with Thymidine
  作者：Bohdan Skalski、Katarzyna Taras-Goślińska、Anna Dembska、Zofia Gdaniec、Stefan Franzen

  DOI：10.1021/jo902136k

  日期：2010.2.5

  Two highly fluorescent, thermally stable diastereomeric photoadducts, 3a,b, are formed when either 5-chloro-4-thiouridine, 1, or 5-fluoro-4-thiouridine, 2, are photoexcited with 366 nm UV light in the presence of thymidine (T). 5-Fluoro-4-thiouridine, 2, exhibits photoreactivity much higher than that of the 5-chloro derivative 1. In both cases the photoreaction is very clean, leading to highly eficient conversion of the 5-halogeno-4-thiouridine (1, 2) and T to photoadducts 3a,b. The identity and structure of 3a was confirmed using mass spectrometry and 2-D NMR. The epimeric relationship of 3a,b was established by UV circular dichroism spectroscopy. The geometry of the fluorescent photoadduct is consistent with formation of an interstrand cross-link in a DNA duplex if 1 or 2 is flanked by T in an opposite strand.