O-(2-(tritylthio)ethyl)hydroxylamine | 1221405-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: O-(2-(tritylthio)ethyl)hydroxylamine
• 英文别名: O-(2-tritylsulfanylethyl)hydroxylamine
• CAS: 1221405-59-9
• 化学式: C₂₁H₂₁NOS
• 分子量: 335.47
• InChiKey: QZMLXXROHOBUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-(2-(tritylthio)ethyl)hydroxylamine 在 三氟乙酸 作用下， 生成 2-Aminooxy-aethylmercaptan
  参考文献：
  名称：

  Peptide ligation assisted by an auxiliary attached to amidyl nitrogen

  摘要：

  New thiol-containing auxiliaries were developed for peptide ligation. They were placed at the amidyl N-atom in the second amino acid residue of a peptide fragment. With the new auxiliaries, peptide ligation could be conducted at non-Cys and non-Gly sites. Compared to other recently developed auxiliaries, an important feature of the present design was that the new auxiliaries were generally applicable and readily removable. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.01.108
• 作为产物：
  描述：

  N-(2-(tritylthio)ethoxy)phthalimide 在 肼 作用下， 以 氯仿 为溶剂， 反应 2.5h， 以90%的产率得到O-(2-(tritylthio)ethyl)hydroxylamine
  参考文献：
  名称：

  天然和蛋白酶抗性泛素化肽的简便合成

  摘要：

  双效泛素化：使用临时连接辅助剂 2-（氨基氧基）乙硫醇将泛素和 SUMO-3 位点特异性地连接到 Lys 侧链 ε-胺。还原后，连接产物是泛素 C 端水解酶 UCH-L3 和 SUMO 特异性蛋白酶 SENP1 的可行底物。泛素化肽中连接辅助剂的保留导致 UCH-L3 抗性类似物。

  DOI：

  10.1002/cbic.201402135

文献信息

• <i>N</i>-<i>tert</i>-Butoxycarbonyl-<i>N</i>-(2-(tritylthio)ethoxy)glycine as a Building Block for Peptide Ubiquitination
  作者：Lingling Peng、Elizabeth Helgason、Rafael Miranda、Jeffrey Tom、Jennifer Zhang、Erin C. Dueber、Aimin Song

  DOI：10.1021/acs.bioconjchem.3c00541

  日期：2024.2.21

  has been developed as a building block for peptide ubiquitination, which is fully compatible with solid-phase Fmoc chemistry and common peptide modifications including phosphorylation, methylation, acetylation, biotinylation, and fluorescence labeling. The optimal conditions for peptide cleavage and auxiliary removal were obtained. The utility of this building block in peptide ubiquitination was demonstrated

  N -Boc- N -(2-(三苯甲基硫基)乙氧基)甘氨酸已被开发为肽泛素化的构建模块，它与固相 Fmoc 化学和常见的肽修饰完全兼容，包括磷酸化、甲基化、乙酰化、生物素化和荧光标记。获得了肽裂解和辅助去除的最佳条件。通过合成七种带有各种修饰的泛素化组蛋白和 Tau 肽，证明了该构建模块在肽泛素化中的实用性。 Cys 残基耐受性良好，不需要正交保护。通过荧光标记的泛素缀合物的酶促去泛素化证实了合成的泛素化肽的结构完整性和折叠。使用该构建模块的合成策略为制备具有多种修饰的泛素化肽提供了实用的方法。
• Solid supports for use in solid-phase peptide synthesis, kits, and related methods
  申请人：UNIVERSITY OF WASHINGTON

  公开号：US10669306B2

  公开（公告）日：2020-06-02

  Solid supports for use in solid-phase peptide synthesis (SPPS) are provided. The solid supports may include a resin and a protected linker coupled to the resin. The linker may be an N-mercaptoethoxyglycine, an N-mercaptopropoxyglycine, an N-mercaptobutoxyglycine, and/or another suitable linker. Kits for use in SPPS are also provided. The kits may include a solid support, a solution including a thiol or a selenol, one or more pluralities of protected amino acids, and/or a wash buffer. Methods of SPPS are also provided. The methods may include providing a solid support including a resin coupled to a protected linker.

  提供了用于固相肽合成（SPPS）的固体支持物。固体支持物可包括树脂和与树脂耦合的受保护连接体。连接体可以是 N-巯基乙氧基甘氨酸、N-巯基丙氧基甘氨酸、N-巯基丁氧基甘氨酸和/或另一种合适的连接体。还提供了用于 SPPS 的试剂盒。这些试剂盒可包括固体支持物、包括硫醇或硒醇的溶液、一种或多种受保护氨基酸和/或洗涤缓冲液。还提供了 SPPS 方法。这些方法可包括提供一种固体支持物，其中包括与受保护连接体偶联的树脂。
• Novel Ligands and Libraries of Ligands
  申请人：Braisted Andrew C.

  公开号：US20120077711A1

  公开（公告）日：2012-03-29

  The present invention provides compounds and libraries of compounds having formula (I): wherein L, n, S and A are defined generally and subsets herein. These compounds and libraries of compounds are useful generally in the drug discovery process.
• SOLID SUPPORTS FOR USE IN SOLID-PHASE PEPTIDE SYNTHESIS, KITS, AND RELATED METHODS
  申请人：UNIVERSITY OF WASHINGTON

  公开号：US20190010186A1

  公开（公告）日：2019-01-10

  Solid supports for use in solid-phase peptide synthesis (SPPS) are provided. The solid supports may include a resin and a protected linker coupled to the resin. The linker may be an N-mercaptoethoxyglycine, an N-mercaptopropoxyglycine, an N-mercaptobutoxyglycine, and/or another suitable linker. Kits for use in SPPS are also provided. The kits may include a solid support, a solution including a thiol or a selenol, one or more pluralities of protected amino acids, and/or a wash buffer. Methods of SPPS are also provided. The methods may include providing a solid support including a resin coupled to a protected linker.
• Peptide ligation assisted by an auxiliary attached to amidyl nitrogen
  作者：Juan Li、Hong-Kui Cui、Lei Liu

  DOI：10.1016/j.tetlet.2010.01.108

  日期：2010.3

  New thiol-containing auxiliaries were developed for peptide ligation. They were placed at the amidyl N-atom in the second amino acid residue of a peptide fragment. With the new auxiliaries, peptide ligation could be conducted at non-Cys and non-Gly sites. Compared to other recently developed auxiliaries, an important feature of the present design was that the new auxiliaries were generally applicable and readily removable. (C) 2010 Elsevier Ltd. All rights reserved.