N-(tertbutyloxycarbonyl)-α-methyl-L-prolyl-L-phenylalanine | 103352-42-7

• 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: N-(tertbutyloxycarbonyl)-α-methyl-L-prolyl-L-phenylalanine
• 英文别名: Boc-aMePro-Phe-OH；(2S)-2-[[(2S)-2-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid
• CAS: 103352-42-7
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: MYVMPNATDLYPIM-YWZLYKJASA-N

物化性质

• 沸点：
  574.9±50.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tertbutyloxycarbonyl)-α-methyl-L-prolyl-L-phenylalanine 在 diethylphosphoryl cyanide 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-L-phenylalanyl>-L-histidyl>-5(S)-amino-4(S)-hydroxy-2(S)-isopropyl-7-methyloctanoyl>-L-isoleucyl>-2-pyridylmethylamine
  参考文献：
  名称：

  .alpha.-Methylproline-containing renin inhibitory peptides: in vivo evaluation in an anesthetized, ganglion-blocked, hog renin infused rat model

  摘要：

  A structure-activity analysis of peptides containing backbone C alpha-methyl modification at the P4 site of the angiotensinogen sequence led to the discovery of potent renin inhibitors with apparent in vitro metabolic stability. Boc-alpha-MePro-Phe-His-Leu psi[CHOHCH2]Val-Ile-Amp dicitrate (Va) is a potent inhibitor of human plasma renin with an IC50 value of 1.8 nM. This peptide was shown not to be degraded in vitro by chymotrypsin, elastase, pepsin, and a rat liver homogenate preparation. It is also a potent inhibitor of hog renin with an IC50 value of 1.6 nM and was shown to elicit in vivo activity and cause dose-dependent hypotensive responses when given intravenously to anesthetized ganglion-blocked, hog renin infused rats.

  DOI：

  10.1021/jm00386a016
• 作为产物：
  描述：

  N-BOC-2-甲基-L-脯氨酸 在 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-(tertbutyloxycarbonyl)-α-methyl-L-prolyl-L-phenylalanine
  参考文献：
  名称：

  .alpha.-Methylproline-containing renin inhibitory peptides: in vivo evaluation in an anesthetized, ganglion-blocked, hog renin infused rat model

  摘要：

  A structure-activity analysis of peptides containing backbone C alpha-methyl modification at the P4 site of the angiotensinogen sequence led to the discovery of potent renin inhibitors with apparent in vitro metabolic stability. Boc-alpha-MePro-Phe-His-Leu psi[CHOHCH2]Val-Ile-Amp dicitrate (Va) is a potent inhibitor of human plasma renin with an IC50 value of 1.8 nM. This peptide was shown not to be degraded in vitro by chymotrypsin, elastase, pepsin, and a rat liver homogenate preparation. It is also a potent inhibitor of hog renin with an IC50 value of 1.6 nM and was shown to elicit in vivo activity and cause dose-dependent hypotensive responses when given intravenously to anesthetized ganglion-blocked, hog renin infused rats.

  DOI：

  10.1021/jm00386a016