(S)-methyl 2-(3,4-diaminobenzamido)-5-guanidinopentanoate | 1295565-41-1

• 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: (S)-methyl 2-(3,4-diaminobenzamido)-5-guanidinopentanoate
• 英文别名: methyl (2S)-2-[(3,4-diaminobenzoyl)amino]-5-(diaminomethylideneamino)pentanoate
• CAS: 1295565-41-1
• 化学式: C₁₄H₂₂N₆O₃
• 分子量: 322.367
• InChiKey: KRRCYWYWJMDVKF-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-(3,4-diaminobenzamido)-5-guanidinopentanoate 、 麦芽七糖 在 碘 、 溶剂黄146 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  标记糖以在质谱分析中增强信号

  摘要：

  MALDI-MS可对大型生物分子（例如蛋白质和核酸）进行快速灵敏的分析。但是，寡糖和多糖在质谱分析中灵敏度较低，部分原因是它们具有中性和亲水性，导致电离效率低。在这项研究中，通过还原末端的适当标签修饰了醛糖，氨基醛糖，醛糖醛酸和α-酮酸这四种低聚糖，以提高其电离效率。缓激肽（BK）是一种血管活性的九肽（RPPGFSPFR），含有两个精氨酸和两个苯丙氨酸残基，被证明是麦芽七糖，GlcNAc低聚物和低聚半乳糖醛酸的出色MS信号增强剂。在以2,5-二羟基苯甲酸（2,5-DHB）为基质的MALDI-TOF-MS分析中，还原胺化制得的GalA4-BK和GalA5-BK结合物的检出限为0.1 fmol，即比未修饰的五内酯酸高约800倍。MS的显着增强归因于碱性精氨酸残基对高质子亲和力和疏水性苯基丙氨酸残基对电离的协同作用。四肽GFGR（OMe）和精氨酸连接的苯二胺（H因此2 N）2 Ph-R（OMe）

  DOI：

  10.1002/jms.1887
• 作为产物：
  描述：

  3,4-二氨基苯甲酸甲酯 在 盐酸胍 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 (S)-methyl 2-(3,4-diaminobenzamido)-5-guanidinopentanoate
  参考文献：
  名称：

  3,4-Diaminobenzoic Acid Derivatives as Inhibitors of the Oxytocinase Subfamily of M1 Aminopeptidases with Immune-Regulating Properties

  摘要：

  Members of the oxytocinase subfamily of M1 aminopeptidases (ERAP1, ERAP2, and IRAP) play important roles in both the adaptive and innate human immune responses. Their enzymatic activity can contribute to the pathogenesis of several major human diseases ranging from viral and parasitic infections to autoimmunity and cancer. We have previously demonstrated that diaminobenzoic acid derivatives show promise as selective inhibitors for this group of aminopeptidases. In this study, we have thoroughly explored a series of 3,4-diaminobenzoic acid derivatives as inhibitors of this class of enzymes, achieving submicromolar inhibitors for ERAP2 (IC50 = 237 nM) and IRAP (IC50 = 105 nM). Cell-based analysis indicated that the lead compounds can be effective in downregulating macrophage activation induced by lipopolysaccharide and interferon-gamma as well as cross-presentation by bone marrow-derived dendritic cells. Our results indicate that this class of inhibitors may be useful for the targeted downregulation of immune responses.

  DOI：

  10.1021/jm501867s

文献信息

• 3,4-Diaminobenzoic Acid Derivatives as Inhibitors of the Oxytocinase Subfamily of M1 Aminopeptidases with Immune-Regulating Properties
  作者：Athanasios Papakyriakou、Efthalia Zervoudi、Sofia Tsoukalidou、Francois-Xavier Mauvais、Georgia Sfyroera、Dimitrios C. Mastellos、Peter van Endert、Emmanuel A. Theodorakis、Dionisios Vourloumis、Efstratios Stratikos

  DOI：10.1021/jm501867s

  日期：2015.2.12

  Members of the oxytocinase subfamily of M1 aminopeptidases (ERAP1, ERAP2, and IRAP) play important roles in both the adaptive and innate human immune responses. Their enzymatic activity can contribute to the pathogenesis of several major human diseases ranging from viral and parasitic infections to autoimmunity and cancer. We have previously demonstrated that diaminobenzoic acid derivatives show promise as selective inhibitors for this group of aminopeptidases. In this study, we have thoroughly explored a series of 3,4-diaminobenzoic acid derivatives as inhibitors of this class of enzymes, achieving submicromolar inhibitors for ERAP2 (IC50 = 237 nM) and IRAP (IC50 = 105 nM). Cell-based analysis indicated that the lead compounds can be effective in downregulating macrophage activation induced by lipopolysaccharide and interferon-gamma as well as cross-presentation by bone marrow-derived dendritic cells. Our results indicate that this class of inhibitors may be useful for the targeted downregulation of immune responses.
• Tagging saccharides for signal enhancement in mass spectrometric analysis
  作者：Yu-Ling Chang、Sylvain Kuo-Shiang Liao、Ying-Chu Chen、Wei-Ting Hung、Hui-Ming Yu、Wen-Bin Yang、Jim-Min Fang、Chung-Hsuan Chen、Yuan Chuan Lee

  DOI：10.1002/jms.1887

  日期：2011.3

  enhancer for maltoheptaose, GlcNAc oligomers and oligogalacturonic acids. In the MALDI‐TOF‐MS analysis using 2,5‐dihydroxybenzoic acid (2,5‐DHB) as the matrix, the GalA4–BK and GalA5–BK conjugates prepared by reductive amination showed the detection limit at 0.1 fmol, i.e. ∼800‐fold enhancement over the unmodified pentagalacturonic acids. The remarkable MS enhancement was attributable to the synergistic

  MALDI-MS可对大型生物分子（例如蛋白质和核酸）进行快速灵敏的分析。但是，寡糖和多糖在质谱分析中灵敏度较低，部分原因是它们具有中性和亲水性，导致电离效率低。在这项研究中，通过还原末端的适当标签修饰了醛糖，氨基醛糖，醛糖醛酸和α-酮酸这四种低聚糖，以提高其电离效率。缓激肽（BK）是一种血管活性的九肽（RPPGFSPFR），含有两个精氨酸和两个苯丙氨酸残基，被证明是麦芽七糖，GlcNAc低聚物和低聚半乳糖醛酸的出色MS信号增强剂。在以2,5-二羟基苯甲酸（2,5-DHB）为基质的MALDI-TOF-MS分析中，还原胺化制得的GalA4-BK和GalA5-BK结合物的检出限为0.1 fmol，即比未修饰的五内酯酸高约800倍。MS的显着增强归因于碱性精氨酸残基对高质子亲和力和疏水性苯基丙氨酸残基对电离的协同作用。四肽GFGR（OMe）和精氨酸连接的苯二胺（H因此2 N）2 Ph-R（OMe）