N-(2-hydroxyethyl)-N-(thymin-1-yl-acetyl)glycine tert-butyl ester | 188779-49-9

• 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: N-(2-hydroxyethyl)-N-(thymin-1-yl-acetyl)glycine tert-butyl ester
• 英文别名: tert-Butyl 2-(N-(2-hydroxyethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetate；tert-butyl 2-[2-hydroxyethyl-[2-(5-methyl-2,4-dioxopyrimidin-1-yl)acetyl]amino]acetate
• CAS: 188779-49-9
• 化学式: C₁₅H₂₃N₃O₆
• 分子量: 341.364
• InChiKey: CSYVFXVWSRSADN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxyethyl)-N-(thymin-1-yl-acetyl)glycine tert-butyl ester 在 吡啶 、 sodium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 N-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-N-({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-carbamoyl}-methyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetamide
  参考文献：
  名称：

  PNA-DNA Chimeras Containing 5-Alkynyl-pyrimidine PNA Units. Synthesis, Binding Properties, and Enzymatic Stability

  摘要：

  Three chimeric dimer synthons (oeg_t(NH)T, oeg_up(NH)T and oeg_uh(NH)T) containing thymine (t), 5-(1-propynyl)-uracil (up) and 5-(1-hexyn-1-yl)-uracil (uh) PNA units with N-(2-hydroxyethyl)glycine (oeg) backbone were synthesized in solution and incorporated into T-20 oligonucleotide analogues, using standard P-amidite chemistry. Insertion of dimer blocks led to destabilization of duplexes with dA(20) target. The smallest T-m drops were found for chimeras containing oeg_up(NH)T dimers. Incorporation of the chimeric synthons into the 3'-end of T-20 brought about growing resistance to 3'-exonucleolytic (SV PDE) cleavage in the order of oeg_t(NH)T < oeg_up(NH)T < oeg_uh(NH)T. Due to different endonuclease activities of 3'- and 5'-exonucleases applied, placing of five consecutive dimers at the 5'-terminus resulted in a relatively smaller, but also side-chain dependent, stabilization towards the hydrolysis by 5'-exonuclease (BS PDE). Neither exonucleases (SV and BS PDE) nor an endonuclease (Nuclease P-1) could hydrolyse the unnatural phosphodiester bond linking the 3'-OH of thymidine to the terminal OH of N-(2-hydroxyethyl)glycine PNA backbone.

  DOI：

  10.1081/ncn-120025243
• 作为产物：
  描述：

  溴乙酸叔丁酯 在 O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 N-(2-hydroxyethyl)-N-(thymin-1-yl-acetyl)glycine tert-butyl ester
  参考文献：
  名称：

  合成PNA单体和PNA-DNA接头分子的新颖途径

  摘要：

  描述了制备可用于合成聚酰胺核酸（PNA）和PNA / DNA嵌合体的由单甲氧基三苯甲基（Mmt）保护的氨基乙基甘氨酸结构单元和由二甲氧基三苯甲基（Dmt）保护的羟乙基甘氨酸衍生物的新方法。用于PNA单体合成的保护基策略可产生易于分离的中间体，最大程度地减少色谱纯化，并适用于大规模单体合成。

  DOI：

  10.1016/s0040-4020(97)01044-2

文献信息

• US5817811A
  申请人：——

  公开号：US5817811A

  公开（公告）日：1998-10-06
• Novel synthetic routes to PNA monomers and PNA-DNA linker molecules
  作者：Gerhard Breipohl、David W. Will、Anusch Peyman、Eugen Uhlmann

  DOI：10.1016/s0040-4020(97)01044-2

  日期：1997.10

  Novel methods for the preparation of monomethoxytrityl (Mmt) protected aminoethylglycine building blocks and dimethoxytrityl (Dmt) protected hydroxyethylglycine derivatives useful for the synthesis of polyamide nucleic acids (PNAs) and PNA/DNA chimeras are described. The protecting group strategy employed for PNA monomer synthesis produces easily isolable intermediates, minimizes chromatographic purification

  描述了制备可用于合成聚酰胺核酸（PNA）和PNA / DNA嵌合体的由单甲氧基三苯甲基（Mmt）保护的氨基乙基甘氨酸结构单元和由二甲氧基三苯甲基（Dmt）保护的羟乙基甘氨酸衍生物的新方法。用于PNA单体合成的保护基策略可产生易于分离的中间体，最大程度地减少色谱纯化，并适用于大规模单体合成。
• PNA-DNA Chimeras Containing 5-Alkynyl-pyrimidine PNA Units. Synthesis, Binding Properties, and Enzymatic Stability
  作者：Zoltán Bajor、Gyula Sági、Zsuzsanna Tegyey†、Ferenc Kraicsovits

  DOI：10.1081/ncn-120025243

  日期：2003.10.1

  Three chimeric dimer synthons (oeg_t(NH)T, oeg_up(NH)T and oeg_uh(NH)T) containing thymine (t), 5-(1-propynyl)-uracil (up) and 5-(1-hexyn-1-yl)-uracil (uh) PNA units with N-(2-hydroxyethyl)glycine (oeg) backbone were synthesized in solution and incorporated into T-20 oligonucleotide analogues, using standard P-amidite chemistry. Insertion of dimer blocks led to destabilization of duplexes with dA(20) target. The smallest T-m drops were found for chimeras containing oeg_up(NH)T dimers. Incorporation of the chimeric synthons into the 3'-end of T-20 brought about growing resistance to 3'-exonucleolytic (SV PDE) cleavage in the order of oeg_t(NH)T < oeg_up(NH)T < oeg_uh(NH)T. Due to different endonuclease activities of 3'- and 5'-exonucleases applied, placing of five consecutive dimers at the 5'-terminus resulted in a relatively smaller, but also side-chain dependent, stabilization towards the hydrolysis by 5'-exonuclease (BS PDE). Neither exonucleases (SV and BS PDE) nor an endonuclease (Nuclease P-1) could hydrolyse the unnatural phosphodiester bond linking the 3'-OH of thymidine to the terminal OH of N-(2-hydroxyethyl)glycine PNA backbone.