Nα-(phenoxyphosphoryl)-L-alanyl-L-proline dipotassium salt | 97280-41-6

• 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: Nα-(phenoxyphosphoryl)-L-alanyl-L-proline dipotassium salt
• 英文别名: N^α-(phenoxyphosphoryl)-L-alanyl-L-proline dipotassium salt
• CAS: 97280-41-6
• 化学式: C₁₄H₁₇N₂O₆P*2K
• 分子量: 418.469
• InChiKey: YHKYANPOTQBRCC-JGAZGGJJSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -3.74
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  121.83
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N^α-(diphenoxyphosphoryl)-L-alanyl-L-proline dicyclobenzylamine salt 在 氢氧化钾 作用下， 以 水 为溶剂， 以85%的产率得到Nα-(phenoxyphosphoryl)-L-alanyl-L-proline dipotassium salt
  参考文献：
  名称：

  N.alpha.-(O,O'-Diphenoxyphosphoryl)-L-alanyl-L-proline, N.alpha.-[O,O'-bis(4-nitrophenoxy)phosphoryl]-L-alanyl-L-proline and N.alpha.-[P-(2-phenylethyl)-O-phenoxyphosphoryl]-L-alanyl-L-proline: releasers of potent inhibitors of angiotensin converting enzyme at physiological pH and temperature

  摘要：

  The rate of loss of phenol or 4-nitrophenol from N alpha-(diphenoxyphosphoryl)-L-alanyl-L-proline (2), N alpha-[bis(4-nitrophenoxy)phosphoryl]-L-alanyl-L-proline (5), and N alpha-[(2-phenylethyl)phenoxyphosphoryl]-L-alanyl-L-proline (12) was determined spectrophotometrically at pH 7.5 and 37 degrees C in both Tris and phosphate buffers. These moderately potent inhibitors of angiotensin converting enzyme (Ki greater than 0.8 microM) all hydrolyze, losing 1 mol of phenol to yield highly potent inhibitors (Ki = 0.5-18 nM). The half-times for loss of 1 mol of phenol in Tris buffer are 22 days (2), 3.4 h (5), and 21 days (12). The half-times in phosphate buffer were not significantly different. The mono(4-nitrophenoxy) ester 6 (Ki = 18 nM) loses its 1 mol of nitrophenol with a half-time of 35 h to yield N alpha-phosphoryl-L-alanyl-L-proline 16 (Ki = 1.4 nM), which hydrolyzes at the P-N bond with a half-time of 2.2 h. Hydrolysis of the P-N bond in 2 and 12 was not observed during the time course of the kinetic experiments. The two phosphoramidate diesters 2 and 5 and the phosphonamidate monoester 12 thus release powerful inhibitors of angiotensin converting enzyme with a known time course at physiological pH and temperature in vitro. A time-dependent increase in inhibitory potency against converting enzyme that paralleled the kinetics of phenyl ester hydrolysis was confirmed in vitro.

  DOI：

  10.1021/jm00148a008