methyl 5(S)-<(tert-butoxycarbonyl)amino>-3(S)-hydroxy-7-methyloctanoate | 86835-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 5(S)-<(tert-butoxycarbonyl)amino>-3(S)-hydroxy-7-methyloctanoate
• 英文别名: methyl 5(S)-[(tert-butoxycarbonyl)amino]-3(S)-hydroxy-7-methyloctanoate
• CAS: 86835-11-2
• 化学式: C₁₅H₂₉NO₅
• 分子量: 303.399
• InChiKey: CBNPFMQUNQONPZ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 methyl 5(S)-<(tert-butoxycarbonyl)amino>-3(S)-hydroxy-7-methyloctanoate 在 吡啶 作用下， 生成 (3S,5S)-5-tert-Butoxycarbonylamino-7-methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octanoic acid methyl ester
  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：

  (1Z)-1-偶氮基-5-甲基-3-({[(2-甲基-2-丙基)氧基]羰基}氨基)-1-己烯-2-醇 在 sodium hydroxide 、 silver benzoate 、 二异丁基氢化铝 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 3.67h， 生成 methyl 5(S)-<(tert-butoxycarbonyl)amino>-3(S)-hydroxy-7-methyloctanoate
  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