methyl N-((5-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate | 216678-84-1

• 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-((5-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate
• 英文别名: methyl 2-[[2-(5-methyl-2-oxo-1H-1,8-naphthyridin-3-yl)acetyl]-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]amino]acetate
• CAS: 216678-84-1
• 化学式: C₂₁H₂₈N₄O₆
• 分子量: 432.477
• InChiKey: PYIKPRYQLLDSAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl N-((5-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate 在 LiOH 作用下， 以 四氢呋喃 、 水 为溶剂， 以53%的产率得到N-((5-methyl-1,8-naphtyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycine
  参考文献：
  名称：

  Peptide nucleic acid monomers and oligomers

  摘要：

  本发明揭示了新型的肽核酸（PNA）寡聚物及其组成单体。这些PNA寡聚物和连接的PNA形成三股结构，与核酸形成三股结构，相对于自然存在的核碱基，在核酸靶点中显示出对胸腺嘧啶的增加特异性。

  公开号：

  US06632919B1
• 作为产物：
  描述：

  2,2-Dimethyl-N-(4-methyl-2-pyridinyl)propanamide 在 盐酸 、 叔丁基锂 、 N,N'-二环己基碳二亚胺 、 lithium diisopropyl amide 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.17h， 生成 methyl N-((5-methyl-1,8-naphthyridin-2(1H)-on-3-yl)acetyl)-N-(2-(tert-butyloxycarbonyl)aminoethyl)glycinate
  参考文献：
  名称：

  Substituted 1,8-Naphthyridin-2(1H)-ones Are Superior to Thymine in the Recognition of Adenine in Duplex as Well as Triplex Structures

  摘要：

  The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degreesC (in separate positions) to 3.5 degreesC (in adjacent positions) in PNA-DNA duplexes and from 1.2 degreesC (in separate positions) to 3.2 degreesC (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degreesC when incorporated into separated and adjacent positions, respectively. Our results furthermore indicate that the duplex stabilization is predominantly enthalpic and therefore most likely not a consequence of single-strand preorganization. Finally, and most surprisingly, we find no direct correlation between the endstacking efficiency of this type of nucleobase and its helix stabilization when involved in Watson-Crick base pairing within a helix.

  DOI：

  10.1021/ja0117027

文献信息

• Peptide nucleic acid monomers and oligomers
  申请人：Nielsen Peter

  公开号：US06632919B1

  公开（公告）日：2003-10-14

  Novel peptide nucleic acid (PNA) oligomers and their constituent monomers are disclosed. The PNA oligomers and linked PNAs form triple stranded structures with nucleic acids that show an increased specificity for thymidine in nucleic acid targets relative to naturally occurring nucleobases.

  本发明揭示了新型的肽核酸（PNA）寡聚物及其组成单体。这些PNA寡聚物和连接的PNA形成三股结构，与核酸形成三股结构，相对于自然存在的核碱基，在核酸靶点中显示出对胸腺嘧啶的增加特异性。
• PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS
  申请人：NIELSEN, Peter Eigil

  公开号：EP0988045B1

  公开（公告）日：2006-02-08
• US6632919B1
  申请人：——

  公开号：US6632919B1

  公开（公告）日：2003-10-14
• Substituted 1,8-Naphthyridin-2(1<i>H</i>)-ones Are Superior to Thymine in the Recognition of Adenine in Duplex as Well as Triplex Structures
  作者：Anne B. Eldrup、Caspar Christensen、Gerald Haaima、Peter E. Nielsen

  DOI：10.1021/ja0117027

  日期：2002.4.1

  The synthesis and evaluation of a series of novel nucleobases based on substituted 1,8-naphthyridin-2(1H)-ones are reported. The nucleobases were designed to meet the requirements for incorporation into peptide nucleic acids (PNAs) and were evaluated as part of PNA duplex and triplex nucleic acid recognition systems. Of the various nucleobases tested, only the 7-chloro-1,8-naphthyridin-2(1H)-one (7-Cl-bT) nucleobase led to consistently increased affinity in all recognition systems, duplex (Watson-Crick) as well as triplex (Hoogsteen). For multiply modified systems, the increase in thermal stability per modification was dependent on the sequence context, ranging from 2.0 degreesC (in separate positions) to 3.5 degreesC (in adjacent positions) in PNA-DNA duplexes and from 1.2 degreesC (in separate positions) to 3.2 degreesC (in adjacent positions) in PNA-RNA duplexes. Singly mismatched oligonucleotide targets were employed to demonstrate uncompromised sequence discrimination. When part of multiply modified triplex (Hoogsteen) recognition systems, the 7-Cl-bT unit gave rise to increases in the thermal stability ranging from 2.7 to 3.5 degreesC when incorporated into separated and adjacent positions, respectively. Our results furthermore indicate that the duplex stabilization is predominantly enthalpic and therefore most likely not a consequence of single-strand preorganization. Finally, and most surprisingly, we find no direct correlation between the endstacking efficiency of this type of nucleobase and its helix stabilization when involved in Watson-Crick base pairing within a helix.