methyl N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycinate | 815645-25-1

• 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 N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycinate
• 英文别名: methyl 2-[[(1S,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopentyl]-[2-[2-oxo-4-(phenylmethoxycarbonylamino)pyrimidin-1-yl]acetyl]amino]acetate
• CAS: 815645-25-1
• 化学式: C₂₇H₃₅N₅O₈
• 分子量: 557.604
• InChiKey: PTCZSLOMQQMQSP-PMACEKPBSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycinate 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以80%的产率得到N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycine
  参考文献：
  名称：

  (S,S)-trans-Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity

  摘要：

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.

  DOI：

  10.1021/ja046280q
• 作为产物：
  描述：

  (1S,2s)-boc-2-氨基环戊烷羧酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 氯甲酸乙酯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 反应 52.91h， 生成 methyl N-[(2S)-tert-butoxycarbonylaminocyclopent-(1S)-yl]-N-[4-N-(benzyloxycarbonyl)cytosin-1-ylacetyl]glycinate
  参考文献：
  名称：

  (S,S)-trans-Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity

  摘要：

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.

  DOI：

  10.1021/ja046280q

文献信息

• (<i>S</i>,<i>S</i>)-<i>trans-</i>Cyclopentane-Constrained Peptide Nucleic Acids. A General Backbone Modification that Improves Binding Affinity and Sequence Specificity
  作者：Jonathan K. Pokorski、Mark A. Witschi、Bethany L. Purnell、Daniel H. Appella

  DOI：10.1021/ja046280q

  日期：2004.11.1

  Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.