methyl (2S,4S)-4-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate | 253307-69-6

• 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: methyl (2S,4S)-4-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate
• CAS: 253307-69-6
• 化学式: C₂₅H₃₂N₄O₇
• 分子量: 500.552
• InChiKey: SOMOGJLXMXSSQU-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S,4S)-4-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以98%的产率得到1-N-(2-(Boc-amino)ethyl)-4S-thymin-1-yl-2S-proline
  参考文献：
  名称：

  Aminoethylprolyl Peptide Nucleic Acids (aepPNA):  Chiral PNA Analogues That Form Highly Stable DNA:aepPNA₂ Triplexes

  摘要：

  [GRAPHICS]The replacement of the glycyl component in the peptide nucleic acid (PNA) backbone by a prolyl unit bearing a nucleobase leads to the aminoethylprolyl (aep) PNAs, which are chiral and cationic. The homooligomeric aepPNA binds to complementary DNA sequences with high affinity and sequence specificity, forming highly stable triplexes.

  DOI：

  10.1021/ol990835i
• 作为产物：
  描述：

  L-羟基脯氨酸 在 氯化亚砜 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 methyl (2S,4S)-4-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Aminoethylprolyl Peptide Nucleic Acids (aepPNA):  Chiral PNA Analogues That Form Highly Stable DNA:aepPNA₂ Triplexes

  摘要：

  [GRAPHICS]The replacement of the glycyl component in the peptide nucleic acid (PNA) backbone by a prolyl unit bearing a nucleobase leads to the aminoethylprolyl (aep) PNAs, which are chiral and cationic. The homooligomeric aepPNA binds to complementary DNA sequences with high affinity and sequence specificity, forming highly stable triplexes.

  DOI：

  10.1021/ol990835i

文献信息

• US7479536B1
  申请人：——

  公开号：US7479536B1

  公开（公告）日：2009-01-20
• Aminoethylprolyl Peptide Nucleic Acids (aepPNA):  Chiral PNA Analogues That Form Highly Stable DNA:aepPNA₂ Triplexes
  作者：Moneesha D'Costa、Vaijayanti A. Kumar、Krishna N. Ganesh

  DOI：10.1021/ol990835i

  日期：1999.11.1

  [GRAPHICS]The replacement of the glycyl component in the peptide nucleic acid (PNA) backbone by a prolyl unit bearing a nucleobase leads to the aminoethylprolyl (aep) PNAs, which are chiral and cationic. The homooligomeric aepPNA binds to complementary DNA sequences with high affinity and sequence specificity, forming highly stable triplexes.