methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate | 226212-75-5

• 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) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate
• 英文别名: (S)-methyl 4-(((benzyloxy)carbonyl)amino)-2-((tertbutoxycarbonyl)amino)butanoate；methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(phenylmethoxycarbonylamino)butanoate
• CAS: 226212-75-5
• 化学式: C₁₈H₂₆N₂O₆
• 分子量: 366.414
• InChiKey: WVBBIFQESBMYTB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以89%的产率得到(S)-benzyl tert-butyl (4-hydroxybutane-1,3-diyl)dicarbamate
  参考文献：
  名称：

  Cγ（S / R）-双峰肽核酸（Cγ- bm- PNA）通过同步结合到两个互补DNA链上形成双双链。

  摘要：

  肽核酸（PNA）是具有中性无环聚酰胺骨架的DNA的线性等价物，该骨架具有通过叔酰胺键连接在氨基乙基甘氨酸重复单元上的核碱基。它们以序列特异性结合互补的DNA或RNA，形成比相应DNA / RNA自双链体更稳定的杂交体。一种新型的PNA称为双峰PNA [Cγ（小号/ [R ）- BM -PNA]被设计成具有通过酰胺垫片附着到侧链上Cγ的重复的第二核碱基AEG PNA寡聚物的单元。已证明每个aeg单元具有两个核碱基的Cγ-双峰PNA低聚物可同时结合两个不同的互补DNA，从两者形成双链体叔酰胺侧和Cγ侧。在此类PNA：DNA三元复合物中，两个双链体共享一个公共的PNA主链。三元DNA 1：Cγ（小号/ [R ）- BM -PNA：DNA 2种复合物显示出比分离的双链体更好的热稳定性，和Cγ（小号） - BM -PNA双链体更稳定比Cγ（[R ）- BM - PNA双工。双峰PNA是可通过天然碱基

  DOI：

  10.1021/acs.joc.0c01853
• 作为产物：
  描述：

  叔丁氧羰基-L-2,4-二氨基丁酸 在 碳酸氢钠 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 methyl (2S) 2-N-tert-butyloxycarbonyl-4-N-benzyloxycarbonyl-(2,4)-diaminobutyrate
  参考文献：
  名称：

  Cγ（S / R）-双峰肽核酸（Cγ- bm- PNA）通过同步结合到两个互补DNA链上形成双双链。

  摘要：

  肽核酸（PNA）是具有中性无环聚酰胺骨架的DNA的线性等价物，该骨架具有通过叔酰胺键连接在氨基乙基甘氨酸重复单元上的核碱基。它们以序列特异性结合互补的DNA或RNA，形成比相应DNA / RNA自双链体更稳定的杂交体。一种新型的PNA称为双峰PNA [Cγ（小号/ [R ）- BM -PNA]被设计成具有通过酰胺垫片附着到侧链上Cγ的重复的第二核碱基AEG PNA寡聚物的单元。已证明每个aeg单元具有两个核碱基的Cγ-双峰PNA低聚物可同时结合两个不同的互补DNA，从两者形成双链体叔酰胺侧和Cγ侧。在此类PNA：DNA三元复合物中，两个双链体共享一个公共的PNA主链。三元DNA 1：Cγ（小号/ [R ）- BM -PNA：DNA 2种复合物显示出比分离的双链体更好的热稳定性，和Cγ（小号） - BM -PNA双链体更稳定比Cγ（[R ）- BM - PNA双工。双峰PNA是可通过天然碱基

  DOI：

  10.1021/acs.joc.0c01853

文献信息

• Synthesis of perhydrodiazepinones as new putative peptidomimetics
  作者：André Nouvet、Marc Binard、Frédéric Lamaty、Jean Martinez、René Lazaro

  DOI：10.1016/s0040-4020(99)00130-1

  日期：1999.4

  New functionalized 7-membered azaheterocycles (perhydrodiazepinones) have been designed as new scaffolds supposed to mimick peptide gamma-turns constrained by an ethylene bridge. They were synthesized by either lactam cyclisation on an aminoacid compound outcoming from a glutamic acid derivative starting material or through an intramolecular Mitsunobu reaction on diaminoalcohol linear precursors. Furthermore, as a new strategy useful for combinatorial chemistry, the second synthesis has been investigated on a soluble polymer support(PEG). (C) 1999 Elsevier Science Ltd. All rights reserved.
• Influence of Pendant Chiral C^γ-(Alkylideneamino/Guanidino) Cationic Side-chains of PNA Backbone on Hybridization with Complementary DNA/RNA and Cell Permeability
  作者：Deepak R. Jain、Libi Anandi V、Mayurika Lahiri、Krishna N. Ganesh

  DOI：10.1021/jo501639m

  日期：2014.10.17

  Intrinsically cationic and chiral CT-substituted peptide nucleic acid (PNA) analogues have been synthesized in the form of gamma(S)-ethyleneamino (eam)- and gamma(S)-ethyleneguanidino (egd)-PNA with two carbon spacers from the backbone. The relative stabilization (Delta T-m.) of duplexes from modified cationic PNAs as compared to 2-aminoethylglycyl (Delta T-m)-PNA is better with complementary DNA (PNA:DNA) than with complementary RNA (PNA:RNA). Inherently, PNA:RNA duplexes have higher stability than PNA:DNA duplexes, and the guanidino PNAs are superior to ' PNAs. The cationic PNAs were found to be specific towl:rd their complementary DNA target as seen from their significantly lower binding with DNA having single base R mismatch. The differential binding avidity of cationic PNAs was assessed by the displacement of DNA duplex intercalated ethidium bromide and gel electrophoresis. The live cell imaging o f amino/guanidino PNA.s demonstrated their ability to penetrate the cell membrane in 3T3 and MCF-7 cells, and cationic PNAs were found to be accumulated in the vicinity of the nuclear membrane in the cytoplasm. Fluorescence activated cell sorter (FACS) analysis of cell permeability showed the efficiency to be dependent upon the nature of cationic functional group, with guanidino PNAs being better than the amino PNAs in both cell lines. The results are useful to design new biofunctional cationic PNA analogues that not only bind RNA better but also show improved cell permeability.