Boc-Phe-Arg(NO2)-OBzl | 32154-91-9

• 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)-OBzl
• 英文别名: Boc-Phe-Arg(NO2)-OBn；benzyl (2S)-5-[[amino(nitramido)methylidene]amino]-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]pentanoate
• CAS: 32154-91-9
• 化学式: C₂₇H₃₆N₆O₇
• 分子量: 556.619
• InChiKey: UWSLAITUOCGIDB-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：

  Boc-Phe-Arg(NO2)-OBzl 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.67h， 生成 benzyl N2-O-benzyl-N-phenylalanyl-L-seryl-L-prolyl-L-phenylalanyl-Nw-nitro-L-argininate
  参考文献：
  名称：

  Synthesis of Des-Pro2-bradykinin and its behavior in chromatography.

  摘要：

  Des-Pro2-缓激肽是通过经典溶液法合成的，作为合成缓激肽中可能存在的污染物的参考化合物，并对其在各种色谱分析中的行为进行了研究。在几种不同条件下的纤维素薄层色谱和纸电泳中，它的Rf值几乎与缓激肽相同，但在特定条件下通过反相高效液相色谱可以明显与缓激肽分离。由于发现Des-Pro2-缓激肽具有显著的缓激肽增强活性，因此在缓激肽合成中应谨慎避免这种物质的污染。

  DOI：

  10.1248/cpb.29.3734
• 作为产物：
  描述：

  BOC-L-苯丙氨酸琥珀酰亚胺酯 、 Nω-nitro-L-arginine benzyl ester 以75%的产率得到
  参考文献：
  名称：

  ROCCHI, R.;BIONDI, L.;FILIRA, F.;SCOLARO, B., INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 2, 240-256

  摘要：

  DOI：

文献信息

• Studies on the Secondary Structure of Bradykinin in Aqueous Solution. Syntheses, Circular Dichroism Spectra, and Biological Activities of Bradykinin Analogs Containing 5-Aminovaleric Acid Residue
  作者：Chikao Hashimoto、Makoto Tamaki、Shosuke Sofuku、Ichiro Muramatsu

  DOI：10.1246/bcsj.64.1533

  日期：1991.5

  of Arg1 and the carboxyl group of Arg9, was proposed for the secondary structure of bradykinin in aqueous solution. The biological activities of these analogs depend on the presence of both Phe residues at positions 5 and 8, and Arg residues at positions 1 and 9. No correlation between the biological activities and the secondary structure could be found.

  通过溶液法合成了八种含有 5-氨基戊酸残基的缓激肽类似物。基于对它们的 CD 谱的考虑，Ser6 的羰基氧和 Phe8 的酰胺质子之间存在分子内 3→1 氢键，Pro2 的羰基氧和 Phe8 的酰胺质子之间存在分子内 4→1 氢键。 Phe5 以及 Arg1 的胍基和 Arg9 的羧基之间的盐桥，被认为是缓激肽在水溶液中的二级结构。这些类似物的生物活性取决于位置 5 和 8 上的 Phe 残基以及位置 1 和 9 上的 Arg 残基的存在。未发现生物活性与二级结构之间的相关性。
• 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.
• ROCCHI, R.;BIONDI, L.;FILIRA, F.;SCOLARO, B., INT. J. PEPTIDE AND PROTEIN RES., 30,(1987) N 2, 240-256
  作者：ROCCHI, R.、BIONDI, L.、FILIRA, F.、SCOLARO, B.

  DOI：——

  日期：——
• Synthesis of Des-Pro2-bradykinin and its behavior in chromatography.
  作者：MASAO NARUSE、KUMIKO YOSHIZAWA、TERUTOSHI KIMURA、SHUMPEI SAKAKIBARA

  DOI：10.1248/cpb.29.3734

  日期：——

  Des-Pro2-Bradykinin was synthesized by the classical solution method as a reference compound for a possible contaminant in synthetic bradykinins, and its behavior in various chromatographic analyses was examined. It showed almost the same Rf values as bradykinin under several different conditions in cellulose thin layer chromatography and in paper electrophoresis, but was clearly separable from bradykinin by reversed phase high performance liquid chromatography under specific conditions. Since des-Pro2-bradykinin was found to have a potent bradykinin-potentiating activity, contamination by this material should be carefully avoided in bradykinin synthesis.

  Des-Pro2-缓激肽是通过经典溶液法合成的，作为合成缓激肽中可能存在的污染物的参考化合物，并对其在各种色谱分析中的行为进行了研究。在几种不同条件下的纤维素薄层色谱和纸电泳中，它的Rf值几乎与缓激肽相同，但在特定条件下通过反相高效液相色谱可以明显与缓激肽分离。由于发现Des-Pro2-缓激肽具有显著的缓激肽增强活性，因此在缓激肽合成中应谨慎避免这种物质的污染。