1-thyminylacetic acid pentafluorophenyl ester | 139166-79-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-thyminylacetic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-Pentafluorophenyl) 2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetate
• CAS: 139166-79-3
• 化学式: C₁₃H₇F₅N₂O₄
• 分子量: 350.202
• InChiKey: HOONSPUYGLNSGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-thyminylacetic acid pentafluorophenyl ester 在 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2S)-3-hydroxy-2-({2-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]acetyl}amino)propanoic acid
  参考文献：
  名称：

  Synthesis of a novel ester analog of nucleic acids bearing a serine backbone

  摘要：

  A novel analog of nucleic acids bearing an optically active serine ester backbone, serine-based nucleobase-linked polyester (SNE), was synthesized. Monomers containing a thymine base were synthesized from L- and D-serines. Furthermore, reaction conditions were thoroughly examined for the ester bond formation by using a new phosphonium-type condensing reagent oil a solid support without racemization. The release of the dimer from the resin was also investigated using a new type of linker, which could be cleaved under neutral conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.076
• 作为产物：
  描述：

  胸腺嘧啶 在 sodium hydroxide 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.17h， 生成 1-thyminylacetic acid pentafluorophenyl ester
  参考文献：
  名称：

  Peptide nucleic acids (PNA). Oligonucleotide analogs with an achiral peptide backbone

  摘要：

  DOI：

  10.1021/ja00031a062

文献信息

• Synthesis and Photochemical Behavior of Peptide Nucleic Acid Dimers and Analogues Containing 4-Thiothymine:  Unprecedented (5−4) Photoadduct Reversion
  作者：Pascale Clivio、Dominique Guillaume、Marie-Thérèse Adeline、Jeanine Hamon、Claude Riche、Jean-Louis Fourrey

  DOI：10.1021/ja971983b

  日期：1998.2.1

  PNA dimers 1−5, containing either 4-thiothymine or N3-methyl-4-thiothymine, were prepared, and the crystal structure of compound 3 was established. With regard to their photochemistry, none of these PNA analogues were able to fully mimic the photochemical behavior observed in the dinucleotide series. Whereas 1 and 2 displayed a sequence dependent photochemistry to give mainly 4-(α-thyminyl) adducts

  制备了含有 4-硫胸腺嘧啶或 N3-甲基-4-硫胸腺嘧啶的 PNA 二聚体 1-5，并确定了化合物 3 的晶体结构。关于它们的光化学，这些 PNA 类似物都不能完全模拟在二核苷酸系列中观察到的光化学行为。虽然 1 和 2 显示出序列依赖的光化学，主要产生 4-(α-胸腺嘧啶) 加合物，但它们的重排异构体 3 和 4 主要产生 (5-4) 光加合物。来自 3 和 4 的光产物显示出在酸性条件下会发生自发逆转为其二胸腺嘧啶母体衍生物。此外，作为该光化学研究的结果，可以表明在溶液中，即使在二聚体阶段，PNA 采用的构象让人联想到 A 型 DNA。
• Duplex strand formation using alternating copolymers
  作者：Hiroshi Nakade、M. Firat IlkerCurrent address: Department of、Brian J. Jordan、Oktay Uzun、Nicholas L. LaPointe、E. Bryan Coughlin、Vincent M. Rotello

  DOI：10.1039/b502929e

  日期：——

  The regular arrangement of complementary diaminopyridine-thymine (DAP-THY) on alternating copolymers permits cooperative binding events and the effective formation of well-controlled micrometre-scale aggregates.

  互补二氨基吡啶-胸腺嘧啶（DAP-THY）在交替共聚物上的规则排列可实现协作结合事件，并有效形成良好控制的微米级聚集体。
• New approach to solid phase synthesis of polyamide nucleic acids analogues (PNA) and PNA-DNA conjugates
  作者：Dmitry A. Stetsenko、Elena N. Lubyako、Viktor K. Potapov、Tatyana L. Azhikima、Evgeny D. Sverdlov

  DOI：10.1016/0040-4039(96)00624-7

  日期：1996.5

  New version of sequential DNA and polyamide solid phase synthesis is applied to the preparation of PNA and PNA-DNA conjugates bearing free 3′-end. N-Mmt protected uracil and thymine PNA monomers are obtained in high yields. Novel support derived from TSK Gel Toyopearl® and efficient coupling procedure with 2,4,6-triisopropylbenzenesulfonyloxy-l-benzotriazole (TPSOBt) are also developed. Preliminary

  新版本的顺序DNA和聚酰胺固相合成技术可用于制备带有3'端的PNA和PNA-DNA共轭物。以高收率获得N-Mmt保护的尿嘧啶和胸腺嘧啶PNA单体。从TSK凝胶的Toyopearl衍生的新的支持®和高效的偶联方法与2,4,6- triisopropylbenzenesulfonyloxy -1-苯并三唑（TPSOBt）也开发。报告了所制备化合物的生物学测试的初步结果。
• Modification of the binding affinity of peptide nucleic acids (PNA). PNA with extended backbones consisting of 2-aminoethyl-β-alanine or 3-aminopropylglycine units
  作者：Birgitte Hyrup、Michael Egholm、Marc Rolland、Peter E. Nielsen、Rolf H. Berg、Ole Buchardt

  DOI：10.1039/c39930000518

  日期：——

  The binding affinity between peptide nucleic acids (PNA) and DNA is reduced by incorporation of PNA units with extended backbones.

  肽核酸（PNA）与DNA之间的结合亲和力通过将PNA单元与扩展的骨架结合而降低。
• Peptide nucleic acids
  申请人：——

  公开号：US20030180734A1

  公开（公告）日：2003-09-25

  A novel class of compounds, known as peptide nucleic acids, bind complementary ssDNA and RNA strands more strongly than a corresponding DNA. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

  一种新型化合物被称为肽核酸，与互补的单链DNA和RNA比相应的DNA更强烈地结合。肽核酸通常包括配体，如天然存在的DNA碱基，通过适当的连接剂连接到肽骨架上。