2-(2-nitrophenyl)-2-((trimethylsilyl)oxy)ethyl 4-methylbenzenesulfonate | 1262031-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-nitrophenyl)-2-((trimethylsilyl)oxy)ethyl 4-methylbenzenesulfonate
• CAS: 1262031-91-3
• 化学式: C₁₈H₂₃NO₆SSi
• 分子量: 409.535
• InChiKey: PFIFBUYUCQLTEH-UHFFFAOYSA-N

物化性质

• 熔点：
  83-87 °C
• 沸点：
  513.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(2-nitrophenyl)-2-((trimethylsilyl)oxy)ethyl 4-methylbenzenesulfonate 在 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Mechanistic Studies on the Substrate-Tolerant Lanthipeptide Synthetase ProcM

  摘要：

  Lanthipeptides are a class of post-translationally modified peptide natural products. They contain lanthionine (Lan) and methyllanthionine (MeLan) residues, which generate cross-links and endow the peptides with various biological activities. The mechanism of a highly substrate-tolerant lanthipeptide synthetase, ProcM, was investigated herein. We report a hybrid ligation strategy to prepare a series of substrate analogues designed to address a number of mechanistic questions regarding catalysis by ProcM. The method utilizes expressed protein ligation to generate a C-terminal thioester of the leader peptide of ProcA, the substrate of ProcM. This thioester was ligated with a cysteine derivative that resulted in an alkyne at the C-terminus of the leader peptide. This alkyne in turn was used to conjugate the leader peptides to a variety of synthetic peptides by copper-catalyzed azide alkyne cycloaddition. Using deuterium-labeled Ser and Thr in the substrate analogues thus prepared, dehydration by ProcM was established to occur from C-to-N-terminus for two different substrates. Cyclization also occurred with a specific order, which depended on the sequence of the substrate peptides. Furthermore, using orthogonal cysteine side-chain protection in the two semisynthetic peptide substrates, we were able to rule out spontaneous non-enzymatic cyclization events to explain the very high substrate tolerance of ProcM. Finally, the enzyme was capable of exchanging protons at the alpha-carbon of MeLan, suggesting that ring formation could be reversible. These findings are discussed in the context of the mechanism of the substrate-tolerant ProcM, which may aid future efforts in lanthipeptide engineering.

  DOI：

  10.1021/ja504692v
• 作为产物：
  描述：

  1-(2-硝基苯基)-1,2-乙二醇 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 19.0h， 生成 2-(2-nitrophenyl)-2-((trimethylsilyl)oxy)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Photochemical cleavage of leader peptides

  摘要：

  我们报告了一种与 Fmoc 固相肽合成和 Cu（I）催化的炔吖啶环加成法兼容的光敏连接体，它可以通过光化学裂解获得具有原生氨基末端的 C 端肽片段。

  DOI：

  10.1039/c0cc02945a

文献信息

• Traceless Purification and Desulfurization of Tau Protein Ligation Products
  作者：Oliver Reimann、Caroline Smet‐Nocca、Christian P. R. Hackenberger

  DOI：10.1002/anie.201408674

  日期：2015.1.2

  for the traceless purification and synthetic modification of peptides and proteins obtained by native chemical ligation. The strategy involves immobilization of a photocleavable semisynthetic biotin–protein conjugate on streptavidin‐coated agarose beads, which eliminates the need for tedious rebuffering steps and allows the rapid removal of excess peptides and additives. On‐bead desulfurization is followed

  我们提出了一种通过天然化学连接获得的肽和蛋白质的无痕纯化和合成修饰的新策略。该策略涉及将光可裂解的半合成生物素-蛋白偶联物固定在链霉亲和素包被的琼脂糖珠上，从而消除了繁琐的重新缓冲步骤，并可以快速去除多余的肽和添加剂。珠上脱硫后，再交付最终的无标签蛋白质产品。从复杂的EPL混合物中分离出无标签的阿尔茨海默氏病相关人类tau蛋白，以及从tau C端衍生的三磷酸化肽，证明了该策略。