2-[[2-[[2-[[2-(5-Methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetic acid | 1026796-74-6

• 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: 2-[[2-[[2-[[2-(5-Methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetic acid
• CAS: 1026796-74-6
• 化学式: C₃₉H₄₅N₉O₁₂
• 分子量: 831.839
• InChiKey: RLFPHBROMFFTQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  60
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  266
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 、 乙酸酐 、 N-[2-(3,4-二氢-5-甲基-2,4-二氧代-1(2H)-嘧啶基)乙酰基]-N-[2-[[(1,1-二甲基乙氧基)羰基]氨基]乙基]-甘氨酸 、 2-[[2-[[2-[[2-(5-Methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetic acid 生成 (2S)-6-amino-2-[[1-hydroxy-2-[2-[[1-hydroxy-2-[2-[[1-hydroxy-2-[[2-[[1-hydroxy-2-[2-[[1-hydroxy-2-[2-[[1-hydroxy-2-[2-(1-hydroxyethylideneamino)ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethylidene]amino]phenyl]methyl-[2-(2-hydroxy-4-iminopyrimidin-1-yl)acetyl]amino]ethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethylidene]amino]hexanimidic acid
  参考文献：
  名称：

  Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

  摘要：

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

  DOI：

  10.1021/jo001650o
• 作为产物：
  描述：

  N-[2-(叔丁氧羰基氨基)乙基]甘氨酸乙酯盐酸盐 在 lithium hydroxide 、 水 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 2-[[2-[[2-[[2-(5-Methyl-2,4-dioxopyrimidin-1-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetyl]amino]phenyl]methyl-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetic acid
  参考文献：
  名称：

  Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA

  摘要：

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.

  DOI：

  10.1021/jo001650o

文献信息

• Backbone Modifications of Aromatic Peptide Nucleic Acid (APNA) Monomers and Their Hybridization Properties with DNA and RNA
  作者：Lee D. Fader、Michael Boyd、Youla S. Tsantrizos

  DOI：10.1021/jo001650o

  日期：2001.5.1

  Aromatic peptide nucleic acid (APNA) monomers containing N-(2-aminobenzyl)-glycine, N-(2-aminobenzyl)-(R)- or -(S)-alanine, and N-(2-aminobenzyl)-beta -alanine moieties as part of their backbone were synthesized. These novel analogues were incorporated as a single "point mutation" in PNA hexamers, and their physicochemical properties were investigated by UV thermal denaturation and CD experiments. Destabilization in tripler formation between the PNA-APNA chimeras and complementary DNA or RNA oligomers was observed, as compared to the PNA control. The APNA monomer composed of the N-(2-aminobenzyl)-glycine backbone led to the smallest decrease in the thermal stability of the triplexes formed with DNA and RNA, while maintaining selectivity for base-pairing recognition. Since the PNA-APNA chimeras are more lipophilic than the corresponding PNA homopolymers, these oligomers may also exhibit better cell membrane permeability properties.