Methyl 2-[2-aminoethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate | 203643-36-1

• 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: Methyl 2-[2-aminoethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate
• CAS: 203643-36-1
• 化学式: C₁₂H₁₈N₄O₅
• 分子量: 298.299
• InChiKey: WWPMGSDLASIMPM-UHFFFAOYSA-N

物化性质

• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-[2-aminoethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate 在 sodium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 {(2-{2-[Benzyloxycarbonyl-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetylamino}-ethyl)-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid
  参考文献：
  名称：

  An expeditious liquid-phase synthesis of cyclic peptide nucleic acids

  摘要：

  Suitably protected linear precursors of cyclic PNAs can be readily obtained by BOP/DiPEA coupling of the corresponding sub-monomers. Conversion of the linear PNA dimers into the pentafluorophenyl esters allows cyclization by intramolecular attack of the deprotected primary amino function under diluted conditions. After removal of the secondary amino protecting group(s), installation of the required nucleobase-acetyl function(s) affords cyclic PNAs. In addition, the latter compounds can be prepared following a direct coupling strategy. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00536-0
• 作为产物：
  描述：

  甘氨酸,N-[(3,4-二氢-5-甲基-2,4-二羰基-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-,甲基酯 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 Methyl 2-[2-aminoethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate
  参考文献：
  名称：

  固体支持物合成的PNA-DNA杂化物

  摘要：

  高硫胸腺嘧啶PNA-DNA八聚体（即杂化物13）的固相支持体合成可以使用N-（2-（4-甲氧基三苯甲基）-氨基乙基）-N -（（胸苷-1-基）乙酰基）甘氨酸盐作为PNA的四丁基铵实现5'- O-（4,4'-二甲氧基三苯甲基）胸苷和5'- N-（4-甲氧基三苯甲基）氨基-5'-脱氧胸苷的结构单元和各自的2-氰基乙基-N，N-二异丙基亚磷酰胺衍生物。

  DOI：

  10.1002/recl.19951140607

文献信息

• Magnetic peptide nucleic acids for DNA targeting
  作者：Giuseppe Prencipe、Stefano Maiorana、Paolo Verderio、Miriam Colombo、Paola Fermo、Enrico Caneva、Davide Prosperi、Emanuela Licandro

  DOI：10.1039/b911449a

  日期：——

  A versatile synthetic platform for the efficient immobilization of PNAs on magnetic iron oxides, providing magnetic nanosensors for selective DNA recognition, is presented.

  提供了一种多功能合成平台，可有效地将PNA固定在磁性氧化铁上，从而为选择性DNA识别提供磁性纳米传感器。
• Synthesis of new building blocks: Towards the analogs of peptide nucleic acids (PNAs)
  作者：Carol Dallaire、Prabhat Arya

  DOI：10.1016/s0040-4039(98)01007-7

  日期：1998.7

  To obtain new analogs of peptide nucleic acids (PNAs), synthesis of the building block 14 has been achieved. Building block 14 has been derived from the coupling of the isothiocyanate derivative, 12 with 13. Isothiocyanate derivative 12 was obtained from S-aspartic acid derivative 5 in a number of steps.

  为了获得肽核酸（PNA）的新类似物，已经实现了构件14的合成。结构单元14已经从异硫氰酸酯衍生物12与13的偶合中得到。从S-天冬氨酸衍生物5通过许多步骤获得异硫氰酸酯衍生物12。
• Transition metal labels on peptide nucleic acid (PNA) monomers
  作者：Alexandra Hess、Nils Metzler-Nolte

  DOI：10.1039/a901561b

  日期：——

  The synthesis, spectroscopic properties (including Mössbauer and electrochemistry) and self-association characteristics of thymine peptide nucleic acid (T–PNA) monomers with covalently linked transition metal markers are described.

  介绍了胸腺嘧啶肽核酸（T-PNA）单体与共价连接的过渡金属标记的合成、光谱特性（包括摩斯鲍尔和电化学）和自结合特性。
• An expeditious liquid-phase synthesis of cyclic peptide nucleic acids
  作者：Jeroen C Verheijen、Gijsbert M Grotenbreg、Ludo Hart de Ruyter、Pieter A.M van der Klein、Gijsbert A van der Marel、Jacques H van Boom

  DOI：10.1016/s0040-4039(00)00536-0

  日期：2000.5

  Suitably protected linear precursors of cyclic PNAs can be readily obtained by BOP/DiPEA coupling of the corresponding sub-monomers. Conversion of the linear PNA dimers into the pentafluorophenyl esters allows cyclization by intramolecular attack of the deprotected primary amino function under diluted conditions. After removal of the secondary amino protecting group(s), installation of the required nucleobase-acetyl function(s) affords cyclic PNAs. In addition, the latter compounds can be prepared following a direct coupling strategy. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Solid support synthesis of a PNA-DNA hybrid
  作者：A. C. van der Laan、N. J. Meeuwenoord、E. Kuyl-Yeheskiely、R. S. Oosting、R. Brands、J. H. van Boom

  DOI：10.1002/recl.19951140607

  日期：——

  The solid support synthesis of a homothymine PNA-DNA octamer (i.e. hybrid 13) could be realized using tetrabutylammonium N-(2-(4-methoxytrityl)-aminoethyl)-N-((thymin-1-yl)acetyl)glycinate as PNA building block and the respective 2-cyanoethyl-N,N-diisopropylphosphoramidite derivatives of both 5′-O-(4,4′-dimethoxytrityl)thymidine and 5′-N-(4-methoxytrityl)amino-5′-deoxythymidine.

  高硫胸腺嘧啶PNA-DNA八聚体（即杂化物13）的固相支持体合成可以使用N-（2-（4-甲氧基三苯甲基）-氨基乙基）-N -（（胸苷-1-基）乙酰基）甘氨酸盐作为PNA的四丁基铵实现5'- O-（4,4'-二甲氧基三苯甲基）胸苷和5'- N-（4-甲氧基三苯甲基）氨基-5'-脱氧胸苷的结构单元和各自的2-氰基乙基-N，N-二异丙基亚磷酰胺衍生物。