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.