thymidylyl-(5'->3')-[5']thymidylic acid | 2642-45-7

• 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: thymidylyl-(5'->3')-[5']thymidylic acid
• 英文别名: 5'-O-Phosphoryl-thymidylyl-(3'-5')-thymidin；5'-Thymidylic acid, thymidylyl-(5'-3')-；[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl [(2R,3S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• CAS: 2642-45-7
• 化学式: C₂₀H₂₈N₄O₁₅P₂
• 分子量: 626.408
• InChiKey: MMXKIWIWQPKTIK-KPRKPIBOSA-N

物化性质

• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  260
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  thymidylyl-(5'->3')-[5']thymidylic acid 在 spleen and snake venom phosphodiesterase 作用下， 生成 胸苷酸
  参考文献：
  名称：

  双（对硝基苯基乙基）磷酸一氯代酯，一种新型多功能磷酸化剂

  摘要：

  已经制备了一种新的磷酸化剂，双-（对-硝基苯基乙基）磷酸一氯代磷酸酯，并用于核苷的3'-和/或5'-磷酸化。所得的双-（对硝基苯基乙基）磷酸三酯是寡核苷酸合成中的通用合成子，最终以优异的产率产生了3'-和/或5'-末端的寡核苷酸。

  DOI：

  10.1016/s0040-4039(00)85715-9
• 作为产物：
  描述：

  3'-O-acetylthymidine 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 thymidylyl-(5'->3')-[5']thymidylic acid
  参考文献：
  名称：

  Studies on Polynucleotides. I. A New and General Method for the Chemical Synthesis of the C₅″-C₃″ Internucleotidic Linkage. Syntheses of Deoxyribo-dinucleotides¹

  摘要：

  DOI：

  10.1021/ja01556a016

文献信息

• PROTECTION OF 5′-TERMINAL PHOSPHATE OF DEOXYRIBOOLIGONUCLEOTIDES BY USE OF o,o′-DIAMINOBIPHENYL
  作者：Makoto Nishizawa、Takashi Kurihara、Tsujiaki Hata

  DOI：10.1246/cl.1984.175

  日期：1984.2.5

  Cyclic phosphorodianilidate derivatives of nucleoside 5′-phosphates were prepared by use of triphenylphosphine and 2,2′-dipyridyl disulfide as condensing agent and used for the synthesis of oligodeoxyribonucleotides. Removal of the diamino group was remarkably accelerated by coaddition of AgOAc and acid anhydrides to the conventional system, iAmONO-pyridine-AcOH.

  以三苯基膦和 2,2'-二硫化二吡啶为缩合剂，制备了 5'-磷酸核苷的环状磷酰二胺衍生物，用于合成寡脱氧核糖核苷酸。通过将 AgOAc 和酸酐共加成到常规体系 iAmONO-吡啶-AcOH 中，显着加速了二氨基的去除。
• Nucleoside und Nucleotide. Teil 14. Synthese des Octanucleosidheptaphosphats d(G-A-T-T-T-T-G-A)
  作者：Peter Bühlmayer、Georg Graf、Felix Waldmeier、Christoph Tamm

  DOI：10.1002/hlca.19800630841

  日期：1980.12.10

  Nucleosides and Nucleotides. Part 14. Synthesis of the Octanucleosideheptaphosphate d(G-A-T-T-T-T-G-A)

  核苷和核苷酸。第14部分。八核苷七磷酸d（GATTTTGA）的合成
• 2-Oxoalkyl caged oligonucleotides: one-electron reductive activation into emergence of ordinary hybridization property by hypoxic X-irradiation
  作者：Kazuhito Tanabe、Hiroshi Kanezaki、Hirotake Ishii、Sei-ichi Nishimoto

  DOI：10.1039/b618810a

  日期：——

  Ionizing radiation triggers the activation of caged oligodeoxynucleotides (ODNs) with a 2-oxoalkyl leaving group to give the corresponding normal uncaged strands. We designed and synthesized ODNs caged by a 2-oxopropyl group at a given thymine N(3) position (doxoT) to evaluate their one-electron reduction characteristics. Upon hypoxic X-radiolysis in aqueous solution, the caged ODNs released the 2-oxopropyl group to produce the corresponding uncaged ODNs. Digestion by a restriction enzyme Swa I revealed that caged ODN pre-irradiated in hypoxia could form an ordinary duplex with its complementary strand.

  电离辐射触发带有 2-氧代烷基离去基团的笼状寡脱氧核苷酸 (ODN) 的激活，产生相应的正常未笼状链。我们设计并合成了在给定胸腺嘧啶 N(3) 位 (doxoT) 处被 2-氧代丙基笼住的 ODN，以评估其单电子还原特性。在水溶液中进行缺氧 X 射线解时，笼状 ODN 释放 2-氧代丙基，产生相应的非笼状 ODN。限制性内切酶Swa I的消化表明，在缺氧条件下预照射的笼养ODN可以与其互补链形成普通双链体。
• Large-Scale Synthesis of Oligonucleotide Phosphorothioates Using 3-Amino-1,2,4-dithiazole-5-thione as an Efficient Sulfur-Transfer Reagent
  作者：Jin-Yan Tang、Yongxin Han、Jimmy X. Tang、Zhaoda Zhang

  DOI：10.1021/op990092g

  日期：2000.5.1

  solid-phase synthesis of oligonucleotide phosphorothioates via the phosphoramidite method. The efficiency of ADTT was investigated by solid-phase syntheses of dinucleotide and oligonucleotide phosphorothioates. The results show that ADTT is a highly efficient sulfur-transfer reagent and fully compatible with automated solid-phase synthesis. ADTT has been applied in manufacture of oligonucleotide phosphorothioates

  一种市售且廉价的化合物 3-氨基-1,2,4-二噻唑-5-硫酮 (ADTT) 被发现是一种新的硫转移试剂，用于通过亚磷酰胺法固相合成寡核苷酸硫代磷酸酯。ADTT 的效率通过二核苷酸和寡核苷酸硫代磷酸酯的固相合成来研究。结果表明，ADTT是一种高效的硫转移试剂，与自动化固相合成完全兼容。ADTT已应用于寡核苷酸硫代磷酸酯的生产，以显着降低成本。
• Unprecedentedly Fast DNA Hydrolysis by the Synergism of the Cerium(IV)-Praseodymium(III) and the Cerium(IV)-Neodymium(III) Combinations
  作者：Naoya Takeda、Takamitsu Imai、Makoto Irisawa、Jun Sumaoka、Morio Yashiro、Hidemi Shigekawa、Makoto Komiyama

  DOI：10.1246/cl.1996.599

  日期：1996.8

  active catalysts for DNA hydrolysis so far have been obtained by using the synergetic cooperation of the cerium(IV) ion with the praseodymium(III) ion. The pseudo first-order rate constant for the hydrolysis of thymidylyl(3′-5′)thymidine by the 2:1 combination is 10 times as great as that by the cerium(IV) ion.

  迄今为止，最活跃的 DNA 水解催化剂是通过使用铈 (IV) 离子与镨 (III) 离子的协同作用获得的。2:1 组合水解胸苷基 (3'-5') 胸苷的拟一级速率常数是铈 (IV) 离子水解的 10 倍。