(S)-2-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester | 347888-69-1

• 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: (S)-2-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-5-oxo-2-(phenylmethoxycarbonylamino)pentanoate
• CAS: 347888-69-1
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: AJADCVOWUCBJDS-AWEZNQCLSA-N

物化性质

• 沸点：
  472.2±45.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester 在 氢溴酸 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 73.0h， 生成 (S)-2-Amino-5-m-tolylamino-pentanoic acid
  参考文献：
  名称：

  Nitroaromatic Amino Acids as Inhibitors of Neuronal Nitric Oxide Synthase

  摘要：

  Nitric oxide (NO .) is an important biomodulator of many physiological processes. The inhibition of inappropriate production of NO . by the isoforms of nitric oxide synthase (NOS) has been proposed as a therapeutic approach for the treatment of stroke, inflammation, and other processes. In this study, certain 2-nitroaryl-substituted amino acid analogues were discovered to inhibit NOS. Analogues bearing a 5-methyl substituent on the aromatic ring demonstrated maximal inhibitory potency. For two selected inhibitors, investigation of the kinetics of the enzyme showed the inhibition to be competitive with L-arginine. Additionally, functional NOS inhibition in tissue preparations was demonstrated.

  DOI：

  10.1021/jm980073h
• 作为产物：
  描述：

  Z-谷安酸叔丁基酯 在 盐酸 、 tris(tert-butoxy)lithium aluminum hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  烯丙基和高烯丙基甘氨酸的立体选择性合成

  摘要：

  从天冬氨酸和谷氨酸衍生物开发了一种新的合成N-保护的烯丙基和高烯丙基甘氨酸的方法。天冬氨酸和谷氨酸衍生物的羧基侧链首先通过与N，O-二甲基羟胺偶联而转化为Weinreb酰胺，然后还原为相应的醛。后者可以与甲基三苯基溴化react反应，以总收率50％得到标题化合物。

  DOI：

  10.1016/s0040-4039(01)00459-2

文献信息

• Stereoselective synthesis of allyl- and homoallylglycines
  作者：Céline Douat、Annie Heitz、Jean Martinez、Jean-Alain Fehrentz

  DOI：10.1016/s0040-4039(01)00459-2

  日期：2001.5

  A new method for the synthesis of N-protected allyl- and homoallylglycines was developed from aspartic and glutamic acid derivatives. The carboxylic side-chains of aspartic and glutamic derivatives was first transformed into the Weinreb amide by coupling with N,O-dimethylhydroxylamine and then reduced into the corresponding aldehyde. The latter could react with methyl-triphenylphosphonium bromide to

  从天冬氨酸和谷氨酸衍生物开发了一种新的合成N-保护的烯丙基和高烯丙基甘氨酸的方法。天冬氨酸和谷氨酸衍生物的羧基侧链首先通过与N，O-二甲基羟胺偶联而转化为Weinreb酰胺，然后还原为相应的醛。后者可以与甲基三苯基溴化react反应，以总收率50％得到标题化合物。
• Nitroaromatic Amino Acids as Inhibitors of Neuronal Nitric Oxide Synthase
  作者：Marlon Cowart、Elizabeth A. Kowaluk、Jerome F. Daanen、Kathy L. Kohlhaas、Karen M. Alexander、Frank L. Wagenaar、James F. Kerwin

  DOI：10.1021/jm980073h

  日期：1998.7.1

  Nitric oxide (NO .) is an important biomodulator of many physiological processes. The inhibition of inappropriate production of NO . by the isoforms of nitric oxide synthase (NOS) has been proposed as a therapeutic approach for the treatment of stroke, inflammation, and other processes. In this study, certain 2-nitroaryl-substituted amino acid analogues were discovered to inhibit NOS. Analogues bearing a 5-methyl substituent on the aromatic ring demonstrated maximal inhibitory potency. For two selected inhibitors, investigation of the kinetics of the enzyme showed the inhibition to be competitive with L-arginine. Additionally, functional NOS inhibition in tissue preparations was demonstrated.