aspartyl-lysyl-proline | 127103-07-5

• 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: aspartyl-lysyl-proline
• 英文别名: AspLysPro；H-Asp-Lys-Pro-OH；(2S)-1-[(2S)-6-amino-2-[[(2S)-2-amino-3-carboxypropanoyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
• CAS: 127103-07-5
• 化学式: C₁₅H₂₆N₄O₆
• 分子量: 358.395
• InChiKey: NZWDWXSWUQCNMG-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.6
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  BocD(OBzl)K(Z)POBzl 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 生成 aspartyl-lysyl-proline
  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

文献信息

• [EN] NOVEL PEPTIDES WITH ANTI-HYPERTENSIVE ACTIVITY<br/>[FR] NOUVEAUX PEPTIDES A ACTIVITE HYPOTENSIVE
  申请人：MONSANTO CO

  公开号：WO2001068114A1

  公开（公告）日：2001-09-20

  Provided are novel tri-peptides which exhibit anti-hypertensive activity. These anti-hypertensive peptides may be used as active ingredients in pharmaceutical compositions, dietary supplements and food ingredients. The present invention also relates to using such novel anti-hypertensive peptides for methods of treatment and prophylaxis of primary hypertension as well as hypertension associated with myocardial infarction, left ventricular systolic dysfunction, diabetes mellitus, progressive renal failure and congestive heart failure.
• Synthesis and activity of NAcSerAspLysPro analogs on cellular interactions between T-cell and erythrocytes in rosette formation
  作者：Josiane Thierry、Marie Pierre Papet、Nathalie Saez-Servent、Jacqueline Plissonneau-Haumont、Pierre Potier、Maryse Lenfant

  DOI：10.1021/jm00170a012

  日期：1990.8

  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.