AEFAEVSK | 840520-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: AEFAEVSK
• CAS: 840520-98-1
• 化学式: C₃₉H₆₁N₉O₁₄
• 分子量: 879.965
• InChiKey: HCMWUCARPGUDDK-AUUUWMTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.42
• 重原子数：
  62.0
• 可旋转键数：
  29.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  387.87
• 氢给体数：
  13.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  AEFAEVSK 、 在 human serum albumin 作用下， 以 aq. phosphate buffer 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  CDDO-咪唑内酯靶向Nrf2衔接子Keap1上的多个氨基酸残基。

  摘要：

  合成的三萜类化合物，包括CDDO，其甲酯（CDDO-Me，巴多索隆甲基）和其咪唑啉（CDDO-Im），通过与衔接蛋白Keap1上的硫醇反应，增强了Nrf2介导的抗氧化和抗炎活性。与单功能CDDO-Me不同，双功能类似物CDDO-Im具有第二个反应位点（咪唑啉），可以与目标蛋白（如谷胱甘肽S-转移酶pi（GSTP），血清白蛋白或半胱氨酸）上的半胱氨酸以外的氨基酸共价结合。 Keap 1。在这里，我们首次显示了低至50 nM的双功能CDDO-Im（与CDDO-Me相反）可以共价转导GSTP中的精氨酸和丝氨酸残基，并将它们交联到相邻的半胱氨酸残基上。此外，我们显示CDDO-Im通过与八个不同的半胱氨酸形成永久的迈克尔加合物而与Keap1共价结合，以及带有赖氨酸和几个酪氨酸残基的酰基加合物。模型研究表明，Tyr 85加合物可稳定Keap1-Cul3复合物，从而增强CDDO-Im的效力。

  DOI：

  10.1021/acs.jmedchem.0c01088
• 作为产物：
  描述：

  human serum albumin 在 碳酸氢铵 、 1,4-二巯基-2,3-丁二醇 、 2-碘乙酰胺 作用下， 反应 0.75h， 生成 AEFAEVSK 、 FQNALLVR 、 DLGEENFK 、 TYETTLEK 、 LVNEVTEFAK 、 LDELRDEGK 、 LCTVATLR 、 FKDLGEENFK 、 YLYEIAR
  参考文献：
  名称：

  Advantages of pyrene derivatization to site-specific glycosylation analysis on MALDI mass spectrometry

  摘要：

  Glycoproteomics involving the analysis of glycopeptides by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) is a new and attractive technique. However, quantitative performance in MALDI-MS is hampered by its poor reproducibility among laser shots. 2,5-Dihydroxybenzoic acid (DHBA) is a useful matrix for glycopeptides but forms highly heterogeneous crystals. In this study, we have investigated the distribution of significant signals generated from a sample of glycopeptides on the target plate using a MALDI imaging technique. MALDI images of glycopeptides, which have different glycans on the same peptide, in the Lys-C digests of bovine ribonuclease B were identical. Thus, all glycoforms on a given peptide can be detected at the same laser irradiation spot simultaneously, which offers a significant advantage over other techniques. A similar result was observed with glycopeptides of human serum immunoglobulin G. Interestingly, distinct MALDI images were observed for glycopeptides having different amino acid sequences, despite having an identical glycan structure. The common peptides, which were glycosylated or non-glycosylated, or sialylated or desialylated gave similar MALDI images. Taken together, our results suggest that sweet spot localization of glycopeptides is dependent on the peptide moiety rather than the glycan structure. Furthermore, introduction of pyrene group to glycopeptides which have different peptides result in a uniform MALDI image. It suggested that pyrene derivatization in MALDI-MS facilitates straightforward analysis of a glycopeptide mixture because the same mass spectrum can be obtained at every sweet spot in addition to increase in signal intensity. Thus, this study validates the use of MALDI-MS for site-specific glycoprofiling at the glycopeptide level. (c) 2012 Published by Elsevier B.V.

  DOI：

  10.1016/j.ijms.2012.08.006

文献信息

• Advantages of pyrene derivatization to site-specific glycosylation analysis on MALDI mass spectrometry
  作者：Takashi Nishikaze、Hisako Okumura、Hiroshi Jinmei、Junko Amano

  DOI：10.1016/j.ijms.2012.08.006

  日期：2013.1

  Glycoproteomics involving the analysis of glycopeptides by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) is a new and attractive technique. However, quantitative performance in MALDI-MS is hampered by its poor reproducibility among laser shots. 2,5-Dihydroxybenzoic acid (DHBA) is a useful matrix for glycopeptides but forms highly heterogeneous crystals. In this study, we have investigated the distribution of significant signals generated from a sample of glycopeptides on the target plate using a MALDI imaging technique. MALDI images of glycopeptides, which have different glycans on the same peptide, in the Lys-C digests of bovine ribonuclease B were identical. Thus, all glycoforms on a given peptide can be detected at the same laser irradiation spot simultaneously, which offers a significant advantage over other techniques. A similar result was observed with glycopeptides of human serum immunoglobulin G. Interestingly, distinct MALDI images were observed for glycopeptides having different amino acid sequences, despite having an identical glycan structure. The common peptides, which were glycosylated or non-glycosylated, or sialylated or desialylated gave similar MALDI images. Taken together, our results suggest that sweet spot localization of glycopeptides is dependent on the peptide moiety rather than the glycan structure. Furthermore, introduction of pyrene group to glycopeptides which have different peptides result in a uniform MALDI image. It suggested that pyrene derivatization in MALDI-MS facilitates straightforward analysis of a glycopeptide mixture because the same mass spectrum can be obtained at every sweet spot in addition to increase in signal intensity. Thus, this study validates the use of MALDI-MS for site-specific glycoprofiling at the glycopeptide level. (c) 2012 Published by Elsevier B.V.
• CDDO-imidazolide Targets Multiple Amino Acid Residues on the Nrf2 Adaptor, Keap1
  作者：Xiaoli Meng、James C. Waddington、Arun Tailor、Adam Lister、Jane Hamlett、Neil Berry、B. Kevin Park、Michael B. Sporn

  DOI：10.1021/acs.jmedchem.0c01088

  日期：2020.9.10

  triterpenoids including CDDO, its methyl ester (CDDO-Me, bardoxolone methyl), and its imidazolide (CDDO-Im) enhance Nrf2-mediated antioxidant and anti-inflammatory activity in many diseases by reacting with thiols on the adaptor protein, Keap1. Unlike monofunctional CDDO-Me, the bifunctional analog, CDDO-Im, has a second reactive site (imidazolide) and can covalently bind to amino acids other than cysteine on

  合成的三萜类化合物，包括CDDO，其甲酯（CDDO-Me，巴多索隆甲基）和其咪唑啉（CDDO-Im），通过与衔接蛋白Keap1上的硫醇反应，增强了Nrf2介导的抗氧化和抗炎活性。与单功能CDDO-Me不同，双功能类似物CDDO-Im具有第二个反应位点（咪唑啉），可以与目标蛋白（如谷胱甘肽S-转移酶pi（GSTP），血清白蛋白或半胱氨酸）上的半胱氨酸以外的氨基酸共价结合。 Keap 1。在这里，我们首次显示了低至50 nM的双功能CDDO-Im（与CDDO-Me相反）可以共价转导GSTP中的精氨酸和丝氨酸残基，并将它们交联到相邻的半胱氨酸残基上。此外，我们显示CDDO-Im通过与八个不同的半胱氨酸形成永久的迈克尔加合物而与Keap1共价结合，以及带有赖氨酸和几个酪氨酸残基的酰基加合物。模型研究表明，Tyr 85加合物可稳定Keap1-Cul3复合物，从而增强CDDO-Im的效力。