benzyl N⁶-((benzyloxy)carbonyl)-L-lysyl-L-prolinate trifluoroacetate | 68280-76-2

• 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: benzyl N⁶-((benzyloxy)carbonyl)-L-lysyl-L-prolinate trifluoroacetate
• 英文别名: H-Lys(Cbz)-Pro-OBn.TFA；benzyl (2S)-1-[(2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoyl]pyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid
• CAS: 68280-76-2
• 化学式: C₂HF₃O₂*C₂₆H₃₃N₃O₅
• 分子量: 581.589
• InChiKey: WEIVANBHXBGMGC-SJEIDVEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Boc-L-天冬氨酸 4-苄酯 、 benzyl N⁶-((benzyloxy)carbonyl)-L-lysyl-L-prolinate trifluoroacetate 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成 BocD(OBzl)K(Z)POBzl
  参考文献：
  名称：

  Synthesis and activity of NAcSerAspLysPro analogs on cellular interactions between T-cell and erythrocytes in rosette formation

  摘要：

  Analogues of NAcSerAspLysPro (AcSDKP), a natural regulator of hematopoiesis isolated from fetal calf bone marrow, were synthesized. The biological activity of these molecules were evaluated in vitro in the rosette assay, which measures the interaction between human Jurkat T-cells and sheep red blood cells. In this test, the tripeptide SerAspLys was the most efficient. Inhibitory activity was detected at the concentration 10(-14) M for the analogue and at 10(-9) M for the parent tetrapeptide. The dipeptide NAcSerAsp still showed activity but at much higher doses (10(-6) M). Substitution of polar amino acids led mostly to inactive molecules. Thus, replacement of Ser by Ala, or Lys by Orn yielded completely inactive compounds and replacement of Asp by Glu decreased the activity (10(-6) M). The present study gives an insight into the role of individual amino acids of AcSDKP in the inhibition of the rosette formation which implicates interactions with T-cell CD2 glycoprotein.

  DOI：

  10.1021/jm00170a012
• 作为产物：
  描述：

  L-脯氨酸苄酯盐酸盐 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， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 benzyl N⁶-((benzyloxy)carbonyl)-L-lysyl-L-prolinate trifluoroacetate
  参考文献：
  名称：

  具有抗白血病活性的Goralatide类似物的合成和生物活性。

  摘要：

  天然四肽Goralatide（AcSDKP）是原始造血细胞增殖的选择性抑制剂。它在体内不稳定，当应用于活细胞时会在4.5分钟内分解。在这项工作中，我们开发了一种Goralatide的类似物，该类似物对人骨髓HL-60，HEL，Nalm-6白血病细胞，内皮HUVEC，胶质母细胞瘤U251和转化的肾293T细胞具有细胞毒性。高拉来肽类似物在有机溶液中显示出显着的稳定性，没有氧化降解的趋势。

  DOI：

  10.1016/j.bmc.2015.04.061

文献信息

• Aminoacid derivatives as antihypertensives
  申请人：ASAHI BREWERIES LTD.

  公开号：EP0279750A2

  公开（公告）日：1988-08-24

  This invention relates to novel aminoacid derivatives which are useful as angiotensin converting enzyme inhibitors.

  本发明涉及可用作血管紧张素转换酶抑制剂的新型氨基酸衍生物。
• NAcSDKP Analogues Resistant to Angiotensin-Converting Enzyme
  作者：Sandrine Gaudron、Marie-Thérèse Adeline、Pierre Potier、Josiane Thierry

  DOI：10.1021/jm9701132

  日期：1997.11.1

  Two series of analogues of the tetrapeptide NAcSDKP, an inhibitor of hematopoietic stem cell proliferation, were prepared, and their enzymatic stability toward rabbit lung angiotensin-converting enzyme (ACE) was evaluated as well as their capacity to inhibit NAcSDKP hydrolysis by this enzyme. In the first series, each of the peptide bonds has been successively replaced by an aminomethylene bond. In the second one, the C-terminus of the peptide has been modified by decarboxylation or amidation. The results reported here indicate that all of these molecules but one have good stability toward the enzyme but none of the compounds is able to inhibit NAcSDKP hydrolysis by ACE.