O-(2-(2-methoxyethoxy)ethyl)-L-serine | 271597-15-0

• 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: O-(2-(2-methoxyethoxy)ethyl)-L-serine
• 英文别名: (2S)-2-azaniumyl-3-[2-(2-methoxyethoxy)ethoxy]propanoate
• CAS: 271597-15-0
• 化学式: C₈H₁₇NO₅
• 分子量: 207.227
• InChiKey: VCZOPZGVTBCUBV-ZETCQYMHSA-N

物化性质

• 沸点：
  345.2±42.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O-(2-(2-methoxyethoxy)ethyl)-L-serine 、 甲氧基-三氟甲基苯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-[2-(2-methoxyethoxy)ethoxy]-2-[(3,3,3-trifluoro-2-methoxy-2-phenylpropionyl)amino]propionic acid
  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
• 作为产物：
  描述：

  1-溴-2-(2-甲氧基乙氧基)乙烷 在 sodium hydride 、 三氟乙酸 作用下， 以 间甲酚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 生成 O-(2-(2-methoxyethoxy)ethyl)-L-serine
  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

• Methods and compositions for controlled polypeptide synthesis
  申请人：——

  公开号：US20020032309A1

  公开（公告）日：2002-03-14

  Methods and compositions for the generation of polypeptides having varied material properties are disclosed herein. Methods include means for initiating the polymerization of aminoacid-N-carboxyanhydride (NCA) monomer by combining the monomer with an amido-containing metallacycle, for making self assembling amphiphilic block copolypeptides and related protocols for adding oligo(ethyleneglycol) functionalized aminoacid-N-carboxyanhydrides (NCAs) to polyaminoacid chains. Additional methods include means of adding an end group to the carboxy terminus of a polyaminoacid chain by reacting an alloc-protected amino acid amide with a transition metal-donor ligand complex to forming an amido-amidate metallacycle for use in further polymerization reactions. Novel compositions for use in peptide synthesis and design including five and six membered amido-containing metallacycles and block copolypeptides are also disclosed.

  本文揭示了用于生成具有不同材料特性的多肽的方法和组合物。方法包括通过将氨基酸-N-羧酸酐（NCA）单体与含有酰胺的金属环结合来启动聚合反应，制备自组装的两性块共聚多肽以及相关的添加寡聚（乙二醇基）功能化氨基酸-N-羧酸酐（NCA）到聚氨基酸链的协议。其他方法包括通过将alloc-保护的氨基酸酰胺与过渡金属给体配体复合物反应，形成酰胺-酰胺金属环，从而向聚氨基酸链的羧基末端添加末端基团，用于进一步的聚合反应。此外，还揭示了用于肽合成和设计的新型组合物，包括五元和六元含酰胺的金属环和块共聚多肽。
• METHODS AND COMPOSITIONS FOR CONTROLLED POLYPEPTIDE SYNTHESIS
  申请人：Deming Timothy J.

  公开号：US20120088848A1

  公开（公告）日：2012-04-12

  Methods and compositions for the generation of polypeptides having varied material properties are disclosed herein. Methods include means for initiating the polymerization of aminoacid-N-carboxyanhydride (NCA) monomer by combining the monomer with an amido-containing metallacycle, for making self assembling amphiphilic block copolypeptides and related protocols for adding oligo(ethyleneglycol) functionalized aminoacid-N-carboxyanhydrides (NCAs) to polyaminoacid chains. Additional methods include means of adding an end group to the carboxy terminus of a polyaminoacid chain by reacting an alloc-protected amino acid amide with a transition metal-donor ligand complex to forming an amido-amidate metallacycle for use in further polymerization reactions. Novel compositions for use in peptide synthesis and design including five and six membered amido-containing metallacycles and block copolypeptides are also disclosed.

  本文揭示了用于生成具有多种材料特性的多肽的方法和组合物。方法包括通过将氨基酸-N-羧酸酐（NCA）单体与含有酰胺基的金属环相结合来启动单体的聚合，以制备自组装的两亲性嵌段共聚多肽，并涉及将寡聚乙二醇功能化的氨基酸-N-羧酸酐（NCAs）添加到聚氨基酸链中的相关协议。另外的方法包括通过将保护的氨基酸酰胺与过渡金属供体配体复合物反应以形成酰胺酰胺金属环，从而向聚氨基酸链的羧基末端添加末端基，以供进一步的聚合反应使用。还揭示了用于肽合成和设计的新型组合物，包括五元和六元含酰胺基的金属环和嵌段共聚多肽。
• US6632922B1
  申请人：——

  公开号：US6632922B1

  公开（公告）日：2003-10-14
• US6686446B2
  申请人：——

  公开号：US6686446B2

  公开（公告）日：2004-02-03
• US7329727B2
  申请人：——

  公开号：US7329727B2

  公开（公告）日：2008-02-12