Boc-L-Arg-^NO2-L-Phe-OBn

• 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: Boc-L-Arg-^NO2-L-Phe-OBn
• 英文别名: Boc-Arg(NO2)-Phe-OBn；benzyl (2S)-2-[[(2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-phenylpropanoate
• 化学式: C₂₇H₃₆N₆O₇
• 分子量: 556.619
• InChiKey: HRKZJRKJBUYIPJ-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  190
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 Boc-L-Arg-^NO2-L-Phe-OBn 反应 1.0h， 以80%的产率得到L-Arg-^NO2-L-Phe-OBn di(trifluoroacetate)
  参考文献：
  名称：

  Selective Inhibition of Neuronal Nitric Oxide Synthase by N^ω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters

  摘要：

  A series of N-omega-nitroarginine (Arg(NO2))-and phenylalanine-containing dipeptides and dipeptide esters were synthesized as potential selective inhibitors of neuronal nitric oxide synthase (nNOS). All of the dipeptides and dipeptide esters are competitive inhibitors of nNOS, macrophage nitric oxide synthase (iNOS), and endothelial nitric oxide synthase (eNOS), except for the ones that contain D-Arg(NO2) (8-10, 12, 13), which are uncompetitive inhibitors of iNOS but competitive inhibitors of nNOS and eNOS. None of the dipeptides or dipeptide esters tested (1, 2, 12, 13) exhibited time-dependent inhibition of any of the NOS isoforms, unlike N-omega-nitro-L-arginine itself, which does, although it is reversible. The order of the amino acids in the dipeptide or dipeptide ester is important to selectivity, and the selectivity depends on the chirality of the amino acids. In the case of the corresponding benzyl esters (5 vs 6), both dipeptides favor iNOS over nNOS and eNOS inhibition. All of the dipeptide methyl esters containing a D-amino acid, however, exhibit an inhibitary preference for nNOS over iNOS and eNOS. The most impressive selectivities observed are 1800- and 800-fold for 12 and 13, respectively, in favour of nNOS over iNOS, unfortunately, the selectivities of these compounds for nNOS over eNOS are only 2.5 and 5.3, respectively.

  DOI：

  10.1021/jm970200u
• 作为产物：
  描述：

  N-Boc-N'-硝基-L-精氨酸 、 3-苯基-L-丙氨酸苄酯 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Boc-L-Arg-^NO2-L-Phe-OBn
  参考文献：
  名称：

  Selective Inhibition of Neuronal Nitric Oxide Synthase by N^ω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters

  摘要：

  A series of N-omega-nitroarginine (Arg(NO2))-and phenylalanine-containing dipeptides and dipeptide esters were synthesized as potential selective inhibitors of neuronal nitric oxide synthase (nNOS). All of the dipeptides and dipeptide esters are competitive inhibitors of nNOS, macrophage nitric oxide synthase (iNOS), and endothelial nitric oxide synthase (eNOS), except for the ones that contain D-Arg(NO2) (8-10, 12, 13), which are uncompetitive inhibitors of iNOS but competitive inhibitors of nNOS and eNOS. None of the dipeptides or dipeptide esters tested (1, 2, 12, 13) exhibited time-dependent inhibition of any of the NOS isoforms, unlike N-omega-nitro-L-arginine itself, which does, although it is reversible. The order of the amino acids in the dipeptide or dipeptide ester is important to selectivity, and the selectivity depends on the chirality of the amino acids. In the case of the corresponding benzyl esters (5 vs 6), both dipeptides favor iNOS over nNOS and eNOS inhibition. All of the dipeptide methyl esters containing a D-amino acid, however, exhibit an inhibitary preference for nNOS over iNOS and eNOS. The most impressive selectivities observed are 1800- and 800-fold for 12 and 13, respectively, in favour of nNOS over iNOS, unfortunately, the selectivities of these compounds for nNOS over eNOS are only 2.5 and 5.3, respectively.

  DOI：

  10.1021/jm970200u

文献信息

• Selective Inhibition of Neuronal Nitric Oxide Synthase by <i>N</i>^ω-Nitroarginine- and Phenylalanine-Containing Dipeptides and Dipeptide Esters
  作者：Richard B. Silverman、Hui Huang、Michael A. Marletta、Pavel Martasek

  DOI：10.1021/jm970200u

  日期：1997.8.1

  A series of N-omega-nitroarginine (Arg(NO2))-and phenylalanine-containing dipeptides and dipeptide esters were synthesized as potential selective inhibitors of neuronal nitric oxide synthase (nNOS). All of the dipeptides and dipeptide esters are competitive inhibitors of nNOS, macrophage nitric oxide synthase (iNOS), and endothelial nitric oxide synthase (eNOS), except for the ones that contain D-Arg(NO2) (8-10, 12, 13), which are uncompetitive inhibitors of iNOS but competitive inhibitors of nNOS and eNOS. None of the dipeptides or dipeptide esters tested (1, 2, 12, 13) exhibited time-dependent inhibition of any of the NOS isoforms, unlike N-omega-nitro-L-arginine itself, which does, although it is reversible. The order of the amino acids in the dipeptide or dipeptide ester is important to selectivity, and the selectivity depends on the chirality of the amino acids. In the case of the corresponding benzyl esters (5 vs 6), both dipeptides favor iNOS over nNOS and eNOS inhibition. All of the dipeptide methyl esters containing a D-amino acid, however, exhibit an inhibitary preference for nNOS over iNOS and eNOS. The most impressive selectivities observed are 1800- and 800-fold for 12 and 13, respectively, in favour of nNOS over iNOS, unfortunately, the selectivities of these compounds for nNOS over eNOS are only 2.5 and 5.3, respectively.