Boc-(2-(2-methoxyethoxy)ethyl)-L-serine | 150438-69-0

• 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: Boc-(2-(2-methoxyethoxy)ethyl)-L-serine
• 英文别名: Nalpha-tert-butyloxycarbonyl-O-(2-(2-methoxyethoxy)ethyl)-L-serine；(2S)-3-[2-(2-methoxyethoxy)ethoxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 150438-69-0
• 化学式: C₁₃H₂₅NO₇
• 分子量: 307.344
• InChiKey: FYBNWOKGUNVEEU-JTQLQIEISA-N

物化性质

• 沸点：
  446.9±45.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Boc-(2-(2-methoxyethoxy)ethyl)-L-serine 在 N-甲基吗啉 、 N,N-二异丙基乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 间甲酚 为溶剂， 反应 0.5h， 生成 3,3,3-trifluoro-N-{2-hydroxy-1-[[2-(2-methoxyethoxy)-ethoxy]methyl]ethyl}-2-methoxy-2-phenylpropionamide
  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：

  (CH3)3Coc(O)nhch(CH2och2CH2och2CH2och3)C(O)OH 以 氯仿 为溶剂， 生成 Boc-(2-(2-methoxyethoxy)ethyl)-L-serine
  参考文献：
  名称：

  Methods and compositions for controlled polypeptide synthesis

  摘要：

  本文公开了用于生成具有不同材料特性的多肽的方法和组合物。其中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结合来启动聚合反应，以制备自组装的两性块状多肽，并包括相关的协议，用于向多肽链中添加寡聚（乙二醇）官能化的氨基酸-N-羧酸酐（NCAs）。另外的方法包括通过将alloc-保护的氨基酸酰胺与过渡金属-给体配合物反应，形成酰胺酰胺金属环，从而向多肽链的羧基端添加末端基，以用于进一步的聚合反应。此外，还公开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块状多肽。

  公开号：

  US06686446B2

文献信息

• CONFORMATIONALLY-PREORGANIZED, MINIPEG-CONTAINING GAMMA-PEPTIDE NUCLEIC ACIDS
  申请人：Ly Danith H.

  公开号：US20140128570A1

  公开（公告）日：2014-05-08

  The present invention relates to γ-PNA monomers according to Formula I where substituent groups R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , B and P are defined as set forth in the specification. The invention also provides methodology for synthesizing compounds according to Formula I and methodology for synthesizing PNA oligomers that incorporate one or more Formula I monomers.

  本发明涉及按照式I定义的γ-PNA单体，其中取代基R1、R2、R3、R4、R5、R6、B和P如规范中所述。本发明还提供了按照式I合成化合物的方法以及合成包含一个或多个式I单体的PNA寡聚物的方法。
• 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