Ethyl (2-(methylthio)ethyl)glycinate | 95200-31-0

• 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: Ethyl (2-(methylthio)ethyl)glycinate
• 英文别名: ethyl 2-(2-methylsulfanylethylamino)acetate
• CAS: 95200-31-0
• 化学式: C₇H₁₅NO₂S
• mdl: MFCD19596334
• 分子量: 177.268
• InChiKey: JRJBJASUXSXUIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl (2-(methylthio)ethyl)glycinate 在 盐酸 、 sodium hydroxide 、 TEA 、 水 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 [(9H-Fluoren-9-ylmethoxycarbonyl)-(2-methylsulfanyl-ethyl)-amino]-acetic acid
  参考文献：
  名称：

  Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P

  摘要：

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2
• 作为产物：
  描述：

  2-(甲硫基)乙胺 、 溴乙酸乙酯 以 四氢呋喃 为溶剂， 生成 Ethyl (2-(methylthio)ethyl)glycinate
  参考文献：
  名称：

  粪肠球菌 Fsr 自诱导肽 (AIP) 的肽-肽混合类似物揭示了重要的结构-活性关系

  摘要：

  将N-烷基甘氨酸衍生物（类肽）纳入粪肠球菌的 GBAP 群体感应信号中揭示了重要的结构功能见解。

  DOI：

  10.1002/cbic.202200527

文献信息

• N,N-substituted azolecarboxamide derivatives useful as fungicides and nematicides
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：EP0121344A2

  公开（公告）日：1984-10-10

  N,N-substituted azolecarboxamide derivatives represented by the formula (I): wherein R, is hydrogen or lower alkyl, Rz is lower alkyl unsubstituted or substituted by lower alkoxy, R3 is lower alkyl, X is a carbon or nitrogen atom, Y is lower alkylene unsubstituted or substituted by lower alkyl and Z is oxygen orsulfur; are useful as fungicides and nematicides.

  由式(I)代表的N，N-取代的唑甲酰胺衍生物： 其中 R, 是氢或低级烷基，Rz 是未被低级烷氧基取代或取代的低级烷基，R3 是低级烷基，X 是碳原子或氮原子，Y 是未被低级烷基取代或取代的低级亚烷基，Z 是氧或硫。
• Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P
  作者：John A. W. Kruijtzer、Lovina J. F. Hofmeyer、Wigger Heerma、Cornelis Versluis、Rob M. J. Liskamp

  DOI：10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2

  日期：1998.8.7

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.
• Peptoid‐Peptide Hybrid Analogs of the <i>Enterococcus faecalis</i> Fsr Auto‐Inducing Peptide (AIP) Reveal Crucial Structure‐Activity Relationships
  作者：Dominic N. McBrayer、Uttam Ghosh、Muralikrishna Lella、Crissey D. Cameron、Yftah Tal‐Gan

  DOI：10.1002/cbic.202200527

  日期：2023.1.3

  The incorporation of N-alkyl glycine derivatives (peptoids) into the GBAP quorum sensing signal in Enterococcus faecalis revealed important structure-function insights.

  将N-烷基甘氨酸衍生物（类肽）纳入粪肠球菌的 GBAP 群体感应信号中揭示了重要的结构功能见解。