benzotriazol-1-yl (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate | 117830-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: benzotriazol-1-yl (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 117830-91-8
• 化学式: C₂₇H₂₅N₅O₅S
• 分子量: 531.592
• InChiKey: XXNUSAHQLVNLNA-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  150
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  、 benzotriazol-1-yl (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate 、 Fmoc-Phe-benzotriazolyl ester 、 Fmoc-Glu(t-Bu)-benzotriazolyl ester 、 (S)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzotriazol-1-yl ester 、 Fmoc-Gly-OBt 、 (S)-3-(4-tert-Butoxy-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid benzotriazol-1-yl ester 在 哌啶 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 1.5h， 以51%的产率得到H-Glu-Tyr-Gly-Ser-Phe-Phe-Cys(Acm)-Glu-Leu-OH
  参考文献：
  名称：

  Synthesis and properties of a new conformational antigen which models an extracellular region of β1-adrenoreceptor

  摘要：

  Two fragments corresponding to the 125-133 and 206-218 sequences of a molecule of the beta 1-adrenoreceptor (autoantibodies to this protein are often found in patients with dilated cardiomyopathy) were synthesized by the solid phase method with the use of Fmoc technology. Two new conformational antigens were prepared by directed (regioselective) and undirected (spontaneous) formation of intramolecular and intermolecular disulfide bridges between the corresponding cysteine residues of the synthesized peptides. One of these antigens consisted of a mixture of disulfide isomers, and another antigen was an isomer with a natural arrangement of S-S bridges. Immunosorbents were obtained by immobilization of the synthesizes antigens on the bromocyanogen-activated sepharose and applied to the removal of autoantibodies in a beta 1-adrenoreceptor from the blood plasma of patients. We demonstrated that the sorbents on the basis of the conformational antigens were more effective in comparison with those containing linear peptide precursors.

  DOI：

  10.1134/s1068162009030029
• 作为产物：
  描述：

  1-羟基苯并三唑 、 芴甲氧羰基-S-乙酰氨甲基-L-半胱氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 0.5h， 生成 benzotriazol-1-yl (2R)-3-(acetamidomethylsulfanyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
  参考文献：
  名称：

  2,2'-二吡啶基二硫化物介导的噻唑烷开环反应在糖蛋白合成中的应用：evasin-3的全化学合成

  摘要：

  噻唑烷开环反应是通过顺序天然化学连接策略进行蛋白质化学合成的关键步骤之一。我们最近开发了一种新的噻唑烷与 2,2'-二吡啶基二硫化物 (DPDS) 的开环反应。为了研究该反应对糖蛋白合成的适用性，我们合成了 evasin-3，这是一种富含半胱氨酸的糖蛋白，具有最初在蜱唾液中发现的趋化因子结合能力。evasin-3的序列分为三个片段，这些片段分别用普通固相肽合成方法合成。在第一次连接中间和 C 端片段后，用作中间片段 N 端 Cys 残基保护基的噻唑烷用 DPDS 转化为 Cys。在这个噻唑烷开环反应中，N-连接的聚糖部分。在与 N 端片段的第二次连接和重折叠反应后，可以以良好的收率获得 evasin-3。合成的 evasin-3 显示出对 CXCL 趋化因子的特异性结合能力。这些结果清楚地表明这种 DPDS 方法可用于糖蛋白合成。

  DOI：

  10.1002/psc.3290

文献信息

• Synthesis and properties of a new conformational antigen which models an extracellular region of β1-adrenoreceptor
  作者：M. V. Sidorova、M. E. Pal’keeva、A. S. Molokoedov、A. A. Az’muko、A. V. Sekridova、M. V. Ovchinnikov、P. A. Levashov、O. I. Afanasieva、Yu. V. Berestetskaya、M. I. Afanasieva、O. A. Razova、Zh. D. Bespalova、S. N. Pokrovskii

  DOI：10.1134/s1068162009030029

  日期：2009.5

  Two fragments corresponding to the 125-133 and 206-218 sequences of a molecule of the beta 1-adrenoreceptor (autoantibodies to this protein are often found in patients with dilated cardiomyopathy) were synthesized by the solid phase method with the use of Fmoc technology. Two new conformational antigens were prepared by directed (regioselective) and undirected (spontaneous) formation of intramolecular and intermolecular disulfide bridges between the corresponding cysteine residues of the synthesized peptides. One of these antigens consisted of a mixture of disulfide isomers, and another antigen was an isomer with a natural arrangement of S-S bridges. Immunosorbents were obtained by immobilization of the synthesizes antigens on the bromocyanogen-activated sepharose and applied to the removal of autoantibodies in a beta 1-adrenoreceptor from the blood plasma of patients. We demonstrated that the sorbents on the basis of the conformational antigens were more effective in comparison with those containing linear peptide precursors.
• Application of 2,2′‐dipyridyl disulfide‐mediated thiazolidine ring‐opening reaction to glycoprotein synthesis: Total chemical synthesis of evasin‐3
  作者：Hidekazu Katayama、Koji Nagata

  DOI：10.1002/psc.3290

  日期：2021.2

  Thiazolidine ring‐opening reaction is one of the key steps in protein chemical synthesis via sequential native chemical ligation strategy. We recently developed a novel thiazolidine ring‐opening reaction with 2,2′‐dipyridyl disulfide (DPDS). In order to investigate the applicability of this reaction to glycoprotein synthesis, we synthesized evasin‐3, a cysteine‐rich glycoprotein with chemokine‐binding

  噻唑烷开环反应是通过顺序天然化学连接策略进行蛋白质化学合成的关键步骤之一。我们最近开发了一种新的噻唑烷与 2,2'-二吡啶基二硫化物 (DPDS) 的开环反应。为了研究该反应对糖蛋白合成的适用性，我们合成了 evasin-3，这是一种富含半胱氨酸的糖蛋白，具有最初在蜱唾液中发现的趋化因子结合能力。evasin-3的序列分为三个片段，这些片段分别用普通固相肽合成方法合成。在第一次连接中间和 C 端片段后，用作中间片段 N 端 Cys 残基保护基的噻唑烷用 DPDS 转化为 Cys。在这个噻唑烷开环反应中，N-连接的聚糖部分。在与 N 端片段的第二次连接和重折叠反应后，可以以良好的收率获得 evasin-3。合成的 evasin-3 显示出对 CXCL 趋化因子的特异性结合能力。这些结果清楚地表明这种 DPDS 方法可用于糖蛋白合成。