KEEPPHHEVPESETC | 360768-40-7

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: KEEPPHHEVPESETC
• 英文别名: PEP 31；H-Lys-Glu-Glu-Pro-Pro-His-His-Glu-Val-Pro-Glu-Ser-Glu-Thr-Cys-OH；(4S)-4-[[(2S)-1-[(2S)-2-[[(2S)-4-carboxy-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-4-carboxy-2-[[(2S)-4-carboxy-2-[[(2S)-2,6-diaminohexanoyl]amino]butanoyl]amino]butanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]butanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]-5-[[(2S)-1-[[(2S)-4-carboxy-1-[[(2S,3R)-1-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 360768-40-7
• 化学式: C₇₃H₁₁₀N₂₀O₂₈S
• 分子量: 1747.86
• InChiKey: YVNZDWOWVYBZKO-QJFORYOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.95
• 重原子数：
  122.0
• 可旋转键数：
  53.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  754.69
• 氢给体数：
  24.0
• 氢受体数：
  27.0

反应信息

• 作为反应物：
  描述：

  2-碘乙酰胺 、 KEEPPHHEVPESETC 反应 1.0h， 生成
  参考文献：
  名称：

  Electrospray ionization mass spectroscopic analysis of peptides modified with N-ethylmaleimide or iodoacetanilide

  摘要：

  The cysteine-specific modifiers we reported previously, N-ethylmaleimide (NEM) and iodoacetanilide (IAA), have been applied to label cysteine residues of peptides in combination with electrospray ionization mass spectrometry (ESI-MS/MS), and their scope in proteomic studies was examined. Peptides modified with N-ethylmaleimide (NEM) or iodoacetanilide (IAA) showed significant enhancement in ionization efficiencies. These modifiers were also found to remain intact in tandem mass spectrometry. Both combinations of N-ethylmaleimide (NEM) and d5-N-ethylmaleimide (d5-NEM), and iodoacetanilide (IAA) and C-13(6)-iodoacetanilide (C-13(6)-IAA) were also shown to be applicable to quantitative analysis of a peptide. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.069

文献信息

• Development of a novel imidazolium-based aromatic quaternary ammonium tag: Synthesis and application to the efficient analysis of cysteinyl-peptides by mass spectrometry
  作者：Xiaoqiang Qiao、Rui Wang、Hongyuan Yan、Tao Wang、Qun Zhao、Lihua Zhang、Yukui Zhang

  DOI：10.1002/rcm.6785

  日期：2014.2.15

  Chemical derivatization is a very promising technique for improving analysis of peptides by mass spectrometry (MS). In this study, a novel kind of imidazolium‐based aromatic quaternary ammonium tag, 1‐[3‐[(2‐iodo‐1‐oxoethyl)amino]propyl]‐3‐butylimidazolium bromide (IPBI), designed with strong gas‐phase basicity and a permanent positive charge, was firstly synthesized and further used for derivatization

  化学衍生化是一种非常有前途的技术，可以改善通过质谱（MS）进行的肽分析。在这项研究中，一种新型的基于咪唑鎓的芳香季铵标签，即1- [3-[（2-碘代-1-氧代乙基）氨基]丙基] -3-丁基咪唑溴化物（IPBI），设计用于强气相首次合成了碱性和永久性正电荷，并进一步用于半胱氨酸肽的衍生化，具有更高的电离效率和更高的电荷态。
• Synthesis of 13C7-labeled iodoacetanilide and application to quantitative analysis of peptides and a protein by isotope differential mass spectrometry
  作者：Satomi Niwayama、Masoud Zabet-Moghaddam、Sadamu Kurono、Hanjoung Cho

  DOI：10.1016/j.bmcl.2009.08.011

  日期：2009.10

  C-13(7)-Labeled iodoacetanilide has been synthesized for specific labeling of sulfhydryl groups of cysteine residues and has been successfully applied to quantitative analysis of peptides and a commercial protein in combination with C-13-unlabeled iodoacetanilide and a MALDI mass spectrometer. Subsequent tandem mass spectrum analysis revealed that C-13(7)-labeled iodoacetanilide remained intact during the collision-induced dissociation ( CID) conditions. (C) 2009 Elsevier Ltd. All rights reserved.