ethyl [N-(N-Boc-pyrrolidin-3-yl-2S-O-TBS-methyl)-N-(2-chloroacetyl)]glycinate | 1444025-53-9

• 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: ethyl [N-(N-Boc-pyrrolidin-3-yl-2S-O-TBS-methyl)-N-(2-chloroacetyl)]glycinate
• CAS: 1444025-53-9
• 化学式: C₂₂H₄₁ClN₂O₆Si
• 分子量: 493.116
• InChiKey: ZPROMWPIFWKUNA-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  85.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl [N-(N-Boc-pyrrolidin-3-yl-2S-O-TBS-methyl)-N-(2-chloroacetyl)]glycinate 在 吡啶 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.75h， 生成 ethyl [N-(N-Boc-pyrrolidin-3-yl-2S-O-mesyl-methyl)-N-(N₁-thyminylacetyl)]glycinate
  参考文献：
  名称：

  C3′-endo-puckered pyrrolidine containing PNA has favorable geometry for RNA binding: Novel ethano locked PNA (ethano-PNA)

  摘要：

  A novel peptide nucleic acid (PNA) analogue is designed with a constraint in the aminoethyl segment of the aegPNA backbone so that the dihedral angle beta is restricted within 60-80 degrees, compatible to form PNA:RNA duplexes. The designed monomer is further functionalized with positively charged amino-/guanidino-groups. The appropriately protected monomers were synthesized and incorporated into aegPNA oligomers at predetermined positions and their binding abilities with cDNA and RNA were investigated. A single incorporation of the modified PNA monomer into a 12-mer PNA sequence resulted in stronger binding with complementary RNA over cDNA. No significant changes in the CD signatures of the derived duplexes of modified PNA with complementary RNA were observed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.015
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯 在 吡啶 、 咪唑 、 sodium tetrahydroborate 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 60.0 ℃ 、275.8 kPa 条件下， 反应 41.0h， 生成 ethyl [N-(N-Boc-pyrrolidin-3-yl-2S-O-TBS-methyl)-N-(2-chloroacetyl)]glycinate
  参考文献：
  名称：

  C3′-endo-puckered pyrrolidine containing PNA has favorable geometry for RNA binding: Novel ethano locked PNA (ethano-PNA)

  摘要：

  A novel peptide nucleic acid (PNA) analogue is designed with a constraint in the aminoethyl segment of the aegPNA backbone so that the dihedral angle beta is restricted within 60-80 degrees, compatible to form PNA:RNA duplexes. The designed monomer is further functionalized with positively charged amino-/guanidino-groups. The appropriately protected monomers were synthesized and incorporated into aegPNA oligomers at predetermined positions and their binding abilities with cDNA and RNA were investigated. A single incorporation of the modified PNA monomer into a 12-mer PNA sequence resulted in stronger binding with complementary RNA over cDNA. No significant changes in the CD signatures of the derived duplexes of modified PNA with complementary RNA were observed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.015