Leu-Leu-Val-Phe-OMe hydrochloride | 24210-22-8

• 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: Leu-Leu-Val-Phe-OMe hydrochloride
• 英文别名: Leu-Leu-Val-Phe-OCH3*HCl；H-Leu-Leu-Val-Phe-OMe.HCl；methyl (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-3-phenylpropanoate;hydrochloride
• CAS: 24210-22-8
• 化学式: C₂₇H₄₄N₄O₅*ClH
• 分子量: 541.131
• InChiKey: IWXPTYRGXJIRFY-JSEXCYGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Leu-Leu-Val-Phe-OMe hydrochloride 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 His-Leu-Leu-Val-Phe-OMe dihydrochloride
  参考文献：
  名称：

  Inhibition of renin by angiotensinogen peptide fragments containing the hydroxy amino acid residue 5-amino-3-hydroxy-7-methyloctanoic acid

  摘要：

  The 3R,5S and 3S,5S diastereoisomers of the hydroxy amino acid 5-amino-3-hydroxy-7-methyloctanoic acid (AHMOA) were synthesized from L-leucine and then incorporated into various peptide fragments of angiotensinogen to give the following polypeptides: AHMOA-Val-Phe-OCH3, His-AHMOA-Val-Phe-OCH3, and AHMOA-Ile-His-OCH3. These compounds were tested in an in vitro renin assay system for their ability to inhibit either hog kidney renin or human amniotic renin. The most active analogue of the series was (3R,5S)-AHMOA-Val-Phe-OCH3 (16). Against hog kidney renin, this compound possessed a Ki = 1.7 X 10(-4) M, while against human amniotic fluid, 16 had a Ki = 0.95 X 10(-4) M. The analogues AHMOA-Val-Phe-OCH3 and His-AHMOA-Val-Phe-OCH3 exhibited noncompetitive kinetics when the 3R,5S isomer of AHMOA was employed and competitive kinetics when the 3S,5S diastereoisomer of AHMOA was used.

  DOI：

  10.1021/jm00364a019
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 Leu-Leu-Val-Phe-OMe hydrochloride
  参考文献：
  名称：

  Leu-Val-Phe-OCH3的N-（α-羟基烷酰基）衍生物作为肾素抑制剂。

  摘要：

  合成以下Leu-Val-Phe-OCH3的N-（α-羟基lakanoyl）衍生物并测试其抑制人羊膜肾素的能力：D-和L-α-羟基异己酰基-Leu-Val-Phe-OCH3，D-和L-α-羟基异戊基-Leu-Val-Phe-OCH3，L-2-羟基-3-苯基丙酰基-Leu-Val-Phe-OCH3以及D-和L-α-羟基苯基乙酰基-Leu-Val-Phe-OCH3 。通过使用Dixion图对化合物的分析显示，所有化合物都是肾素的竞争性抑制剂。发现除D-α-羟基异戊基-Leu-Val-Phe-OCH3以外的所有化合物都比已知的四肽抑制剂Leu-Leu-Val-Phe-OCH3更具活性（1）。该系列中两个活性最高的化合物是L-α-羟基异己酰基-Leu-Val-Phe-OCH3（Ki = 0.23 mM）和L-α-羟基异戊酰基-Leu-Val-Phe-OCH3（Ki = 0.3 mM）。

  DOI：

  10.1021/jm00180a017

文献信息

• N-(.alpha.-hydroxyalkanoyl) derivatives of Leu-Val-Phe-OCH3 as inhibitors of renin
  作者：Rodney L. Johnson

  DOI：10.1021/jm00180a017

  日期：1980.6

  The following N-(alpha-hydroxylakanoyl) derivatives of Leu-Val-Phe-OCH3 were synthesized and tested for their ability to inhibit human amniotic renin: D- and L-alpha-hydroxyisocaproyl-Leu-Val-Phe-OCH3, D- and L-alpha-hydroxyisovaleryl-Leu-Val-Phe-OCH3, L-2-hydroxy-3-phenylpropanoyl-Leu-Val-Phe-OCH3, and D- and L-alpha-hydroxyphenylacetyl-Leu-Val-Phe-OCH3. Analysis of the compounds through the use of

  合成以下Leu-Val-Phe-OCH3的N-（α-羟基lakanoyl）衍生物并测试其抑制人羊膜肾素的能力：D-和L-α-羟基异己酰基-Leu-Val-Phe-OCH3，D-和L-α-羟基异戊基-Leu-Val-Phe-OCH3，L-2-羟基-3-苯基丙酰基-Leu-Val-Phe-OCH3以及D-和L-α-羟基苯基乙酰基-Leu-Val-Phe-OCH3 。通过使用Dixion图对化合物的分析显示，所有化合物都是肾素的竞争性抑制剂。发现除D-α-羟基异戊基-Leu-Val-Phe-OCH3以外的所有化合物都比已知的四肽抑制剂Leu-Leu-Val-Phe-OCH3更具活性（1）。该系列中两个活性最高的化合物是L-α-羟基异己酰基-Leu-Val-Phe-OCH3（Ki = 0.23 mM）和L-α-羟基异戊酰基-Leu-Val-Phe-OCH3（Ki = 0.3 mM）。
• Inhibition of renin by angiotensinogen peptide fragments containing the hydroxy amino acid residue 5-amino-3-hydroxy-7-methyloctanoic acid
  作者：Rodney L. Johnson、Karen Verschoor

  DOI：10.1021/jm00364a019

  日期：1983.10

  The 3R,5S and 3S,5S diastereoisomers of the hydroxy amino acid 5-amino-3-hydroxy-7-methyloctanoic acid (AHMOA) were synthesized from L-leucine and then incorporated into various peptide fragments of angiotensinogen to give the following polypeptides: AHMOA-Val-Phe-OCH3, His-AHMOA-Val-Phe-OCH3, and AHMOA-Ile-His-OCH3. These compounds were tested in an in vitro renin assay system for their ability to inhibit either hog kidney renin or human amniotic renin. The most active analogue of the series was (3R,5S)-AHMOA-Val-Phe-OCH3 (16). Against hog kidney renin, this compound possessed a Ki = 1.7 X 10(-4) M, while against human amniotic fluid, 16 had a Ki = 0.95 X 10(-4) M. The analogues AHMOA-Val-Phe-OCH3 and His-AHMOA-Val-Phe-OCH3 exhibited noncompetitive kinetics when the 3R,5S isomer of AHMOA was employed and competitive kinetics when the 3S,5S diastereoisomer of AHMOA was used.