4-nitrophenyl L-prolinate hydrochloride | 25024-46-8

• 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: 4-nitrophenyl L-prolinate hydrochloride
• CAS: 25024-46-8
• 化学式: C₁₁H₁₂N₂O₄*ClH
• 分子量: 272.688
• InChiKey: RIZSOYYGYNIYQH-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.47
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl L-prolinate hydrochloride 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成
  参考文献：
  名称：

  Oxo-ester Mediated Native Chemical Ligation: Concept and Applications

  摘要：

  A direct oxo-ester peptide ligation method has been developed. Through the use of an activated C-terminal para nitrophenyl ester (1), it is possible to achieve direct cysteine ligations (1 + 2 -> 4). Peptide substrates incorporating bulky C-terminal amino acids (1) can be accommodated with high reaction efficiency.

  DOI：

  10.1021/ja804993y
• 作为产物：
  描述：

  Boc-Pro-ONp 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-nitrophenyl L-prolinate hydrochloride
  参考文献：
  名称：

  Oxo-ester Mediated Native Chemical Ligation: Concept and Applications

  摘要：

  A direct oxo-ester peptide ligation method has been developed. Through the use of an activated C-terminal para nitrophenyl ester (1), it is possible to achieve direct cysteine ligations (1 + 2 -> 4). Peptide substrates incorporating bulky C-terminal amino acids (1) can be accommodated with high reaction efficiency.

  DOI：

  10.1021/ja804993y

文献信息

• Solid-phase total synthesis of cyclic peptide brachystemin A and its immunomodulating activity
  作者：Zafar Ali SHAH、Almas JABEEN、Samreen SOOMRO、M. Ahmed MESAIK、M. Iqbal CHOUDHARY、Farzana SHAHEEN

  DOI：10.3906/kim-1412-58

  日期：——

  Brachystemin A (\textbf1}) is a biologically active peptide from a Chinese traditional plant \textitBrachystemma calycinum} D. Don. (Caryophyllaceae). The current study describes the complete solid-phase total synthesis of peptide \textbf1} by using Kenner's sulfonamide safety-catch linker strategy. It was identified by QTOF/MS data and NMR studies. Synthetic peptide \textbf1} was tested for its immunomodulatory effect on different inflammatory parameters, including production of inflammatory cytokines, interleukin 2 (IL-2), tumor necrosis factor-$\alpha $ (TNF-$\alpha )$, and interleukin-1$\beta $ (IL-1$\beta )$, and generation of nitric oxide (NO$^.})$. The synthetic peptide \textbf1} showed a moderate to low level of inhibition on the production of IL-2 (35.2\%}), TNF-$\alpha $ (19.3\%}), and IL-1$\beta $(7.5\%}) at a concentration of 25 $\mu $M. The effect of the compound on viability of cells was also evaluated, and it was found to be nontoxic on 3T3 cells.

  Brachystemin A (\textbf1}) 是一种来源于中国传统植物\textitBrachystemma calycinum} D. Don.（石竹科）的生物活性肽。本研究通过采用Kenner硫酰胺安全捕捉链接策略，实现了该肽的全固相总合成，并通过QTOF/MS数据和NMR研究进行了鉴定。合成的肽\textbf1}针对不同炎症参数，包括炎症细胞因子的产生、白细胞介素2（IL-2）、肿瘤坏死因子-$\alpha $（TNF-$\alpha ）$、白细胞介素-1$\beta $（IL-1$\beta ）$和一氧化氮生成，进行了免疫调节效应测试。在25 $\mu $M浓度下，合成的肽\textbf1}对IL-2（35.2\%）、TNF-$\alpha $（19.3\%）和IL-1$\beta $（7.5\%）的产生显示出中度至低水平的抑制作用。同时，该化合物对细胞活力的影响也进行了评估，结果表明对3T3细胞无毒性。