[(9H-Fluoren-9-ylmethoxycarbonyl)-(2-methylsulfanyl-ethyl)-amino]-acetic acid | 171856-10-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [(9H-Fluoren-9-ylmethoxycarbonyl)-(2-methylsulfanyl-ethyl)-amino]-acetic acid
• 英文别名: 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}[2-(methylsulfanyl)ethyl]amino)acetic acid；2-[9H-fluoren-9-ylmethoxycarbonyl(2-methylsulfanylethyl)amino]acetic acid
• CAS: 171856-10-3
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: KTEBMUVOMKNIMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  硫代异氰酸苯酯 、 [(9H-Fluoren-9-ylmethoxycarbonyl)-(2-methylsulfanyl-ethyl)-amino]-acetic acid 生成 1-(2-Methylsulfanyl-ethyl)-3-phenyl-2-thioxo-imidazolidin-4-one
  参考文献：
  名称：

  通过埃德曼降解法对类肽拟肽进行测序

  摘要：

  描述了通过测序直接鉴定树脂结合的类肽拟肽。用异硫氰酸苯酯处理拟肽的N-末端，然后从树脂上裂解N-末端拟肽残基作为其硫代乙内酰脲衍生物。为了推导类肽序列，将获得的巯基乙内酰脲的HPLC保留时间与独立制备的参考巯基乙内酰脲的HPLC保留时间进行了比较。

  DOI：

  10.1016/s0040-4039(98)00556-5
• 作为产物：
  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

文献信息

• 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。