2'-deoxy-4-thiouridylyl(3'-5')thymidine | 124763-40-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 2'-deoxy-4-thiouridylyl(3'-5')thymidine
• 英文别名: 5'-O-(2'-deoxy-4-thiouridylyl)thymidine；s4Ura-dRibf-P-dThd；[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-2-(hydroxymethyl)-5-(2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-3-yl] hydrogen phosphate
• CAS: 124763-40-2
• 化学式: C₁₉H₂₅N₄O₁₁PS
• 分子量: 548.467
• InChiKey: ZEVSWXYJNYJJTE-SWTKMSQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  229
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2'-deoxy-4-thiouridylyl(3'-5')thymidine 以 水 为溶剂， 生成 、
  参考文献：
  名称：

  NMR and molecular modelling studies of two photoproducts of 2′-deoxy-4- thiouridylyl-(3′,5′)- thymidine.

  摘要：

  Preparation, spectroscopic analysis and molecular modelling of dYo(4-alpha;p)dT and dhs4U(6-alpha;p)dT, two photoproducts of 2'-deoxy-4-thiouridylyl-(3',5')-thymidine are described. The 6(S) configuration of the additional chiral centre of dhs4U(6-alpha;p)dT has been determined using 2D-NMR spectroscopy. NMR data also provided conformational information on the deoxyribose and glycosidic torsion angles of dYo(4-alpha;p)dT and dhs4U(6-alpha;p)dT. The two fragments of dYo(4-a;p)dT have an anti type glycosidic conformation. The furanose conformation of the 5'-end is exclusively C3' -endo and that of -pdT is mainly C2' -endo. A syn/anti glycosidic torsion angle is found for both sugars in dhs4U(6-alpha;p)dT. A C2' -endo/C3' -endo conformation blend exists for the 5' -furanose whereas the second sugar prefers a C2' -endo geometry. The detailed three-dimensional reconstruction of the solution state was performed using NMR guided molecular modelling.

  DOI：

  10.1016/s0040-4020(01)88719-6
• 作为产物：
  描述：

  在 溶剂黄146 作用下， 反应 0.5h， 生成 2'-deoxy-4-thiouridylyl(3'-5')thymidine
  参考文献：
  名称：

  Clivio, Pascale; Fourrey, Jean-Louis; Gasche, Jeanette, Journal of the Chemical Society. Perkin transactions I, 1992, # 18, p. 2383 - 2388

  摘要：

  DOI：

文献信息

• γ-Radiolysis DNA Products:  Synthesis of 6-(α-Thyminyl)-5,6-dihydro-4-thiothymine Derivatives
  作者：Javier Ulises Ortiz Mayo、François-Yves Dupradeau、Dominique Guillaume、Jean-Louis Fourrey、Pascale Clivio

  DOI：10.1021/jo0401570

  日期：2004.7.1

  radical [6-(α-thyminyl) derivative]. In the latter series, two stereochemical pathways took place during the reaction between the methylene and C6 radicals. The major pathway occurred when the 5‘-base glycosidic bond had an anti conformation leading to an S configuration of the C6 Tp-end. The minor pathway, which had never been reported before in this series, involved a 5‘-base in a syn conformation leading

  4-硫代胸苷基（3'-5'）胸苷的远紫外光解导致形成三种稳定的衍生物：一种是由3'端亚甲基与5'端C 4自由基结合而成的[4- （α-胸腺嘧啶基）衍生物]和两个在3'端亚甲基基团和5'端C 6基团[6-（α-胸苷基）衍生物]结合后形成。在后一个系列中，亚甲基和C 6自由基之间的反应过程中发生了两个立体化学途径。当5'-碱基糖苷键具有反式构象导致C 6的S构型时，发生了主要途径TP结束。在该系列之前从未报道过的次要途径涉及一个5'碱基的顺式构象，从而导致C 6 Tp端的R构型。这两个加合物的5，6-二氢胸腺嘧啶部分呈现5，6-反式双轴取代，这是由5，6-二氢嘧啶5-位差向异构化的顺式-二取代中间体进行差向异构化而产生的。
• Sequence dependent photochemistry of di(deoxynucleoside) phosphates containing 4-thiouracil
  作者：Jean-Louis Fourrey、Jeannette Gasche、Catherine Fontaine、Eric Guittet、Alain Favre

  DOI：10.1039/c39890001334

  日期：——

  The photochemistry of (dideoxynucleoside) phosphates (4c) and (4d) is strictly sequence dependent.

  （双脱氧核苷）磷酸盐（4c）和（4d）的光化学严格取决于序列。