N^α-tert-Butoxycarbonyl-6-cyano-D,L-norleucine | 177031-12-8

• 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: N^α-tert-Butoxycarbonyl-6-cyano-D,L-norleucine
• 英文别名: 2-{[(Tert-butoxy)carbonyl]amino}-6-cyanohexanoic acid；6-cyano-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 177031-12-8
• 化学式: C₁₂H₂₀N₂O₄
• 分子量: 256.302
• InChiKey: CMQMDJLHJZYEPN-UHFFFAOYSA-N

物化性质

• 沸点：
  463.0±40.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  99.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N^α-tert-Butoxycarbonyl-6-cyano-D,L-norleucine 在 苄基三乙基氯化铵 、 羟胺 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 为溶剂， 反应 28.0h， 生成 N^α-tert-Butoxycarbonyl-N^ω-hydroxy-D,L-indospicine tert-butyl ester
  参考文献：
  名称：

  Synthesis and effects on arginase and nitric oxide synthase of two novel analogues of N^ω-hydroxyarginine, N^ω-hydroxyindospicine and p-hydroxyamidinophenylalanine

  摘要：

  Two novel amino acids, N-omega-hydroxy-D,L-indospicine and p-hydroxyamidino-D,L-phenylalanine, have been synthesized in four steps from tert-butoxycarbonylglycine. Both compounds act as good inhibitors of arginase, N-omega-hydroxyindospicine being one of the best inhibitors of this enzyme known so far (IC50 = 50 mu mol dm(-3)). In contrast, with brain NO synthase the two compounds are almost without effect.

  DOI：

  10.1039/p19960000645
• 作为产物：
  描述：

  BOC-甘氨酸 、 5-溴戊腈 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 N^α-tert-Butoxycarbonyl-6-cyano-D,L-norleucine
  参考文献：
  名称：

  Synthesis and effects on arginase and nitric oxide synthase of two novel analogues of N^ω-hydroxyarginine, N^ω-hydroxyindospicine and p-hydroxyamidinophenylalanine

  摘要：

  Two novel amino acids, N-omega-hydroxy-D,L-indospicine and p-hydroxyamidino-D,L-phenylalanine, have been synthesized in four steps from tert-butoxycarbonylglycine. Both compounds act as good inhibitors of arginase, N-omega-hydroxyindospicine being one of the best inhibitors of this enzyme known so far (IC50 = 50 mu mol dm(-3)). In contrast, with brain NO synthase the two compounds are almost without effect.

  DOI：

  10.1039/p19960000645