Pro-Phe-Arg | 23846-09-5

• 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: Pro-Phe-Arg
• 英文别名: Prolylphenylalanylarginine；(2S)-5-(diaminomethylideneamino)-2-[[(2S)-3-phenyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]propanoyl]amino]pentanoic acid
• CAS: 23846-09-5
• 化学式: C₂₀H₃₀N₆O₄
• 分子量: 418.496
• InChiKey: LGMBKOAPPTYKLC-JYJNAYRXSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-2-[(S)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxamido]-3-phenylpropanoic acid 在 palladium on activated charcoal N-乙基马来酰亚胺 、 sodium hydroxide 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 36.0h， 生成 Pro-Phe-Arg
  参考文献：
  名称：

  Tri- and tetrapeptide analogs of kinins as potential renal vasodilators

  摘要：

  Tri- and tetrapeptide analogues were synthesized and evaluated as renal vasodilators. These peptides were prepared by standard coupling reactions, which also provided good yields with hindered alpha-methyl amino acid derivatives. Preliminary evidence of renal vasodilator activity was determined in anesthetized dogs by measuring the effects on renal blood flow and calculating the accompanying changes in renal vascular resistance. The most potent compounds contained, in their basic structure, the L-prolyl-DL-alpha-methylphenylalanyl-L-arginine and L-prolyl-DL-alpha-methylphenylalanylglycyl-L-proline arrays. Substitution on the N-terminal proline with 4-phenylbutyryl and 4-(4-hydroxyphenyl)butyryl side chains produced enhanced renal vasodilator activity and, in certain cases, selectivity for the renal vasculature.

  DOI：

  10.1021/jm00369a017

文献信息

• Oligopeptide derivatives of ipoxantine endowed with immunomodulating activity and pharmaceutical compositions containing same
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0464009A2

  公开（公告）日：1992-01-02

  Ipoxantine derivatives of general formula (I): both as racemate and chiral forms and the salts thereof with pharmacologically acceptable cations, wherein n is an integer comprised between 2 and 6, and A is the residue of a dipeptide, tripeptide, tetrapeptide and pentapeptide selected, respectively, from the groups consisting of: (a) glycyl-aspartate, alanyl-glycine, glycyl-glycine, aspartyl-arginine, leucyl-arginine; (b) arginyl-lysyl-aspartate, aspartyl-lysyl-arginine, lysyl-prolyl-arginine, prolyl-prolyl-arginine, lysyl-histidyl-glycinamide, prolyl-phenilalanyl-arginine, phenylalanyl-prolyl-arginine; (c) arginyl-lysyl-aspartyl-valine, valyl-aspartyl-lysyl-arginine, threonylvalyl-leucyl-histidyne; and (d) arginyl-lysyl-aspartyl-valyl-tyrosine; are endowed with immunomodulating activity and can be formulated in orally or parenterally administrable pharmaceutical compositions.

  通式(I)的次黄嘌呤衍生物： 外消旋体和手性体及其与药理学上可接受的阳离子的盐类，其中 n 是介于 2 和 6 之间的整数，A 是二肽、三肽、四肽和五肽的残基，分别选自由下列组成的组 (a) 甘氨酰-天冬氨酸、丙氨酰-甘氨酸、甘氨酰-甘氨酸、天冬氨酰-精氨酸、亮氨酰-精氨酸； (b) 精氨酰-赖氨酰-天冬氨酸、天冬氨酰-赖氨酰-精氨酸、赖氨酰-脯氨酰-精氨酸、脯氨酰-脯氨酰-精氨酸、赖氨酰-组氨酰-甘氨酰胺、脯氨酰-苯丙氨酰-精氨酸、苯丙氨酰-脯氨酰-精氨酸； (c) 精氨酰-赖氨酰-天冬氨酰-缬氨酸、缬氨酰-天冬氨酰-赖氨酰-精 氨酰、苏氨酰-缬氨酰-亮氨酰-组氨酰；以及 (d) 精氨酰-赖氨酰-天冬氨酰-缬氨酰-酪氨酸；具有免疫调节活性，可配制成口服或肠外给药的药物组合物。
• Immunological tolerance inducing agent
  申请人：Hamajima, Fusanori

  公开号：EP0771869A1

  公开（公告）日：1997-05-07

  An SH-dependent protease is disclosed which is obtainable by crushing placentae of a mammal to thereby obtain a homogenate, centrifuging the homogenate and subjecting the resultant supernatant to affinity chromatography (I), ion exchange chromatography, gel filtration chromatography and affinity chromatography (II) in this order and which has the following physicochemical properties. Function: cleaving L-prolyl-L-phenylalanyl-L-arginine 4-methyl-coumaryl-7-amide to produce L-prolyl-L-phenylalanyl-L-arginine and 7-amino-4-methyl-coumarin; Optimum pH range: 5.6 - 6.5; Range of optimum temperature: 36.5 - 37.5 °C; Stability: retaining its activity at -80 °C for at least 30 days in 5 mM acetate buffer (pH 5.0), and being completely denatured on heating at 100°C for 3 minutes; Molecular weight: 30 kDa. An immunological tolerance inducing-agent comprising the SH-dependent protease as an active ingredient is also provided.

  本发明公开了一种 SH 依赖性蛋白酶，可通过粉碎哺乳动物的胎盘以获得匀浆，离心匀浆并将所得上清液依次进行亲和层析 (I)、离子交换层析、凝胶过滤层析和亲和层析 (II) 而获得，该蛋白酶具有以下理化性质。 功能：裂解 L-脯氨酰-L-苯丙氨酰-L-精氨酸 4-甲基香豆素-7-酰胺，生成 L-脯氨酰-L-苯丙氨酰-L-精氨酸和 7-氨基-4-甲基香豆素；最佳 pH 值范围：最佳 pH 值范围：5.6 - 6.5；最佳温度范围：36.5 - 37.5 °C稳定性：在 5 毫摩尔醋酸盐缓冲液（pH 5.0）中-80 °C 下保持活性至少 30 天，100 °C加热 3 分钟后完全变性；分子量：30 kDa。 还提供了一种免疫耐受诱导剂，其活性成分包括 SH 依赖性蛋白酶。
• Aminoacyl and oligopeptidyl derivatives of allopurinol exhibiting immunostimulatory activity, and pharmaceutical formulations containing these substances
  申请人：Sigma-Tau Industrie Farmaceutiche Riunite S.p.A.

  公开号：EP0506628B1

  公开（公告）日：1996-09-18
• METHODS FOR TREATMENT OF DISORDERS OF CARDIAC CONTRACTILITY
  申请人：JOHNS HOPKINS UNIVERSITY

  公开号：EP1044002A1

  公开（公告）日：2000-10-18
• EP1044002A4
  申请人：——

  公开号：EP1044002A4

  公开（公告）日：2003-05-02