Boc-Phe-Arg(NO2)-OH | 17461-58-4

• 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-Phe-Arg(NO2)-OH
• 英文别名: (2S)-5-[[amino(nitramido)methylidene]amino]-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoic acid
• CAS: 17461-58-4
• 化学式: C₂₀H₃₀N₆O₇
• 分子量: 466.494
• InChiKey: XXOJBQOZYNOJKR-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  33
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  201
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Arg(NO2)-OH 在 三氟乙酸 作用下， 生成 N^ω-nitro-N^α-L-phenylalanyl-L-arginine
  参考文献：
  名称：

  Vinogradova,E.I. et al., Journal of general chemistry of the USSR, 1970, vol. 40, p. 1371 - 1382

  摘要：

  DOI：
• 作为产物：
  描述：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 在 sodium hydroxide 、 三乙胺 作用下， 生成 Boc-Phe-Arg(NO2)-OH
  参考文献：
  名称：

  Vinogradova,E.I. et al., Journal of general chemistry of the USSR, 1970, vol. 40, p. 1371 - 1382

  摘要：

  DOI：

文献信息

• Novel substrates for use in measuring the concentration of kallikrein in
  申请人：Nitto Boseki Co., Ltd.

  公开号：US04650753A1

  公开（公告）日：1987-03-17

  A novel chromogenic and fluorescent substrate for measuring the concentration of kallikrein in urine. The novel substrate according to the present invention has very excellent substrate specificity to kallikreins and good solubility in water or biological test solutions. The present substrate is therefore useful for measuring the concentration of kallikrein in urine for the diagnosis of hypertension and other diseases caused by the lowering of the concentration of kallikrein.

  一种新型的色原和荧光底物，用于测定尿中卡利肯酶的浓度。根据本发明的新型底物对卡利肯酶具有非常优异的底物特异性，并且在水或生物测试溶液中具有良好的溶解性。因此，该底物对于测定尿中卡利肯酶的浓度，以诊断由卡利肯酶浓度降低引起的高血压和其他疾病非常有用。
• 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.