L-精氨酸酰胺,N-[(苯基甲氧基)羰基]-L-苯基丙氨酰-N-(4-硝基苯基)- | 117761-01-0

• 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
• 中文名称: L-精氨酸酰胺,N-[(苯基甲氧基)羰基]-L-苯基丙氨酰-N-(4-硝基苯基)-
• 英文名称: Z-Phe-Arg-pNA
• 英文别名: benzyloxycarbonyl-Phe-Arg-p-nitroanilide；Cbz-Phe-Arg-pNA；Z-FR-pNA；benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-(4-nitroanilino)-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 117761-01-0
• 化学式: C₂₉H₃₃N₇O₆
• 分子量: 575.624
• InChiKey: SNRRZRWIWHSYLU-DQEYMECFSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  207
• 氢给体数：
  5
• 氢受体数：
  7

制备方法与用途

Z-Phe-Arg-pNA是组织蛋白酶L的底物。

反应信息

• 作为反应物：
  描述：

  L-精氨酸酰胺,N-[(苯基甲氧基)羰基]-L-苯基丙氨酰-N-(4-硝基苯基)- 在 papain 、 1,4-二巯基-2,3-丁二醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-硝基苯胺
  参考文献：
  名称：

  Selective chromogenic and fluorogenic peptide substrates for the assay of cysteine peptidases in complex mixtures

  摘要：

  This study describes the design, synthesis, and use of selective peptide substrates for cysteine peptidases of the Cl papain family, important in many biological processes. The structure of the newly synthesized substrates is Glp-Xaa-Ala-Y (where Glp = pyroglutamyl; Xaa = Phe or Val; and Y = pNA [p-nitroanilide], AMC [4-amino-7-methylcoumaride], or AFC [4-amino-7-trifluoromethyl-coumaridel]). Substrates were synthesized enzymatically to guarantee selectivity of the reaction and optical purity of the target compounds, simplifying the scheme of synthesis and isolation of products. The hydrolysis of the synthesized substrates was evaluated by C1 cysteine peptidases from different organisms and with different functions, including plant enzymes papain, bromelain, ficin, and mammalian lysosomal cathepsins B and L. The new substrates were selective for C1 cysteine peptidases and were not hydrolyzed by serine, aspartic, or metallo peptidases. We demonstrated an application of the selectivity of the synthesized substrates during the chromatographic separation of a multicomponent set of digestive peptidases from a beetle, Tenebrio molitor. Used in combination with the cysteine peptidase inhibitor E-64, these substrates were able to differentiate cysteine peptidases from peptidases of other classes in midgut extracts from T. molitor larvae and larvae of the genus Tribolium; thus, they are useful in the analysis of complex mixtures containing peptidases from different classes. Published by Elsevier Inc.

  DOI：

  10.1016/j.ab.2013.12.032

文献信息

• FORMULATION FOR ORAL ADMINISTRATION OF PROTEINS
  申请人：Immunogenics LLC

  公开号：EP2321640B1

  公开（公告）日：2016-11-30
• RAPID DETECTION OF SULFHYDRYL COMPOUNDS USING A PAPAIN BASED ASSAY
  申请人：Flint Dennis

  公开号：US20100022018A1

  公开（公告）日：2010-01-28

  The invention relates to a method for detecting compounds containing a free sulfhydryl group in a sample and a test device which is used to detect such compounds. The method and test device use a papain-based assay where the papain is initially complexed with a metal ion making it inactive. Sulfydryl compounds in a sample activate the papain. Enzymatic activity of papain on a papain substrate releases a dye producing a detectable signal. The test device may be used in detecting compounds containing a free sulfhydryl group in industrial, environmental, experimental and biological samples.
• Formulation for Oral Administration of Proteins
  申请人：Siegel Matthew John

  公开号：US20110171201A1

  公开（公告）日：2011-07-14

  Pharmaceutical formulations of orally administered proteins can be stabilized from oxidative degradation and inactivation in the stomach and GI tract by the addition of an antioxidant.
• US8980254B2
  申请人：——

  公开号：US8980254B2

  公开（公告）日：2015-03-17
• US9993531B2
  申请人：——

  公开号：US9993531B2

  公开（公告）日：2018-06-12