Boc-(2-(2-methoxyethoxy)ethyl)-L-serine guanine(Cbz) | 1312415-92-1

• 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: Boc-(2-(2-methoxyethoxy)ethyl)-L-serine guanine(Cbz)
• 英文别名: 2-[[(2R)-3-[2-(2-methoxyethoxy)ethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-[2-[6-oxo-2-(phenylmethoxycarbonylamino)-1H-purin-9-yl]acetyl]amino]acetic acid
• CAS: 1312415-92-1
• 化学式: C₃₀H₄₁N₇O₁₁
• 分子量: 675.696
• InChiKey: TWJFINIWXUTWFC-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  221
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Boc-(2-(2-methoxyethoxy)ethyl)-L-serine guanine(Cbz) 在 sodium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  含手性γ-肽核酸单体的光不稳定SPhNPPOC保护的（R）-MiniPEG的合成与表征

  摘要：

  肽核酸（PNA）微阵列有望被开发为新一代的基因检测工具。然而，不良的水溶性和非手性PNA探针的序列设计的局限性主要阻碍了它们的应用。因此，（R为了解决这些问题，已经开发了含有手性PNA（miniPEG-γPNA）的1，2-二甘醇。导光合成是制备高密度微阵列的有效方法。噻吩-2-（2-硝基苯基）丙氧羰基（SPhNPPOC）是一种新合成的具有高光解效率的光不稳定保护基。用SPhNPPOC保护PNA单体可通过光导合成改善PNA微阵列的制备过程，从而缩短了脱保护时间并抑制了副反应。在本文中，合成了受SPhNPPOC /碳苯甲氧基（Cbz）保护的手性miniPEG-γPNA单体，其光脱保护速率约为2-（2-硝基苯基）丙氧基羰基（NPPOC）保护的单体的两倍。

  DOI：

  10.1071/ch20017
• 作为产物：
  描述：

  1-溴-2-(2-甲氧基乙氧基)乙烷 在 N-甲基吗啉 、 正丙胺 、 偶氮二甲酸二异丙酯 、 水 、 sodium hydride 、 3-羟基-1,2,3-苯并三嗪-4(3H)-酮 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 29.58h， 生成 Boc-(2-(2-methoxyethoxy)ethyl)-L-serine guanine(Cbz)
  参考文献：
  名称：

  Synthesis and Characterization of Conformationally Preorganized, (R)-Diethylene Glycol-Containing γ-Peptide Nucleic Acids with Superior Hybridization Properties and Water Solubility

  摘要：

  Developed in the early 1990s, peptide nucleic acid (PNA) has emerged as a promising class of nucleic acid mimic because of its strong binding affinity and sequence selectivity toward DNA and RNA and resistance to enzymatic degradation by proteases and nucleases; however, the main drawbacks, as compared to other classes of oligonucleotides, are water solubility and biocompatibility. Herein we show that installation of a relatively small, hydrophilic (R)-diethylene glycol ("miniPEG", R-MP) unit at the gamma-backbone transforms a randomly folded PNA into a right-handed helix. Synthesis of optically pure (R-MP)gamma PNA monomers is described, which can be accomplished in a few simple steps from a commercially available and relatively cheap Boc-L-serine. Once synthesized, (R-MP)gamma PNA oligomers are preorganized into a right-handed helix, hybridize to DNA and RNA with greater affinity and sequence selectivity, and are more water soluble and less aggregating than the parental PNA oligomers. The results presented herein have important implications for the future design and application of PNA in biology, biotechnology, and medicine, as well as in other disciplines, including drug discovery and molecular engineering.

  DOI：

  10.1021/jo200482d

文献信息

• Synthesis and characterization of (R)-miniPEG-containing chiral γ-peptide nucleic acids using the Fmoc strategy
  作者：Bo Dong、Kaixuan Nie、Huanhuan Shi、Xiaoxia Yao、Lemeng Chao、Bo Liang、Zhengchun Liu

  DOI：10.1016/j.tetlet.2019.04.038

  日期：2019.5

  (miniPEG)-containing chiral γPNA is considered to be one of the best PNA derivatives. Its preparation is mainly based on the Boc strategy for solid phase peptide synthesis (SPPS), requiring the repeated use of trifluoroacetic acid TFA, which is not suitable for the in situ synthesis of PNA arrays and some other applications under mild conditions. Herein, Fmoc/Cbz orthogonal protected miniPEG-containing chiral γPNA

  含二甘醇（miniPEG）的手性γPNA被认为是最好的PNA衍生物之一。它的制备主要基于Boc固相肽合成（SPPS）策略，需要重复使用三氟乙酸TFA，这不适用于PNA阵列的原位合成以及在温和条件下的其他一些应用。本文合成了Fmoc / Cbz正交保护的含miniPEG的手性γPNA单体，并在温和条件下使用Fmoc策略制备了15merγPNA。
• Synthesis and Characterization of Conformationally Preorganized, (<i>R</i>)-Diethylene Glycol-Containing γ-Peptide Nucleic Acids with Superior Hybridization Properties and Water Solubility
  作者：Bichismita Sahu、Iulia Sacui、Srinivas Rapireddy、Kimberly J. Zanotti、Raman Bahal、Bruce A. Armitage、Danith H. Ly

  DOI：10.1021/jo200482d

  日期：2011.7.15

  Developed in the early 1990s, peptide nucleic acid (PNA) has emerged as a promising class of nucleic acid mimic because of its strong binding affinity and sequence selectivity toward DNA and RNA and resistance to enzymatic degradation by proteases and nucleases; however, the main drawbacks, as compared to other classes of oligonucleotides, are water solubility and biocompatibility. Herein we show that installation of a relatively small, hydrophilic (R)-diethylene glycol ("miniPEG", R-MP) unit at the gamma-backbone transforms a randomly folded PNA into a right-handed helix. Synthesis of optically pure (R-MP)gamma PNA monomers is described, which can be accomplished in a few simple steps from a commercially available and relatively cheap Boc-L-serine. Once synthesized, (R-MP)gamma PNA oligomers are preorganized into a right-handed helix, hybridize to DNA and RNA with greater affinity and sequence selectivity, and are more water soluble and less aggregating than the parental PNA oligomers. The results presented herein have important implications for the future design and application of PNA in biology, biotechnology, and medicine, as well as in other disciplines, including drug discovery and molecular engineering.
• Synthesis and Characterisation of Photolabile SPhNPPOC-Protected (R)-MiniPEG Containing Chiral γ-Peptide Nucleic Acid Monomers
  作者：Qingteng Lai、Bo Dong、Kaixuan Nie、Huanhuan Shi、Bo Liang、Zhengchun Liu

  DOI：10.1071/ch20017

  日期：——

  effective method to fabricate high-density microarrays. Thiophenyl-2-(2-nitrophenyl)propoxycarbonyl (SPhNPPOC) is a newly synthesised photolabile protective group with high photolytic efficiency. Protecting the PNA monomers with SPhNPPOC may improve the preparation process of PNA microarrays by light-directed synthesis in terms of shortening the deprotection time and restraining side reactions. In this article

  肽核酸（PNA）微阵列有望被开发为新一代的基因检测工具。然而，不良的水溶性和非手性PNA探针的序列设计的局限性主要阻碍了它们的应用。因此，（R为了解决这些问题，已经开发了含有手性PNA（miniPEG-γPNA）的1，2-二甘醇。导光合成是制备高密度微阵列的有效方法。噻吩-2-（2-硝基苯基）丙氧羰基（SPhNPPOC）是一种新合成的具有高光解效率的光不稳定保护基。用SPhNPPOC保护PNA单体可通过光导合成改善PNA微阵列的制备过程，从而缩短了脱保护时间并抑制了副反应。在本文中，合成了受SPhNPPOC /碳苯甲氧基（Cbz）保护的手性miniPEG-γPNA单体，其光脱保护速率约为2-（2-硝基苯基）丙氧基羰基（NPPOC）保护的单体的两倍。