Glutamyl-histidyl-prolinamide

• 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: Glutamyl-histidyl-prolinamide
• 英文别名: (4S)-4-amino-5-[[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₆H₂₄N₆O₅
• 分子量: 380.404
• InChiKey: CDKISEMTCDQDIY-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  185
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Glutamyl-histidyl-prolinamide 在 Tris-HCl buffer 作用下， 60.0 ℃ 、800.0 MPa 条件下， 生成 大鼠转铁蛋白
  参考文献：
  名称：

  Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus

  摘要：

  Peptides containing the cyclic product of glutamine at the N terminus are usually biologically active. If the cyclization of glutamine was associated with a volume reduction, pressure should displace the equilibrium in the direction of the lower volume. Here, results in model solutions and in whey are discussed, showing that the theorized cyclization of glutamine in Gln-His-ProNH(2) or Gln-Leu-ProNH(2) is significantly accelerated during the application of heat and even more strongly when elevated temperature and pressure combinations are used. The reaction rate depended on the intensity of the pressure treatment, the pH, and the nature of the amino acids adjacent to glutamine. The products of the reaction were identified as thyrotropin-releasing hormone (TRH) and [Leu(2)]TRH. The reported reactions could affect the naturally balanced concentration of short-chain peptides in foods and therefore induce unpredictable biological effects.

  DOI：

  10.1021/jf0348471
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 CBZ-L-焦谷氨酸 、 N-Boc-N'-苄氧甲基-L-组氨酸 生成 Glutamyl-histidyl-prolinamide
  参考文献：
  名称：

  Hydrolytic Cleavage of Pyroglutamyl-Peptide Bond. IV. Highly Selective Cleavage of Thyrotropin Releasing Hormone (TRH) in Aqueous Methanesulfonic Acid.

  摘要：

  本文描述了促甲状腺激素释放激素（TRH）（pGlu-His-Pro-NH2）在多种条件下在各种酸中的酸水解以及 pGlu-His 键的高选择性裂解。首先，研究了 TRH 在稀酸中的分解。将 TRH 在 60°C 的 1 N HCl 中培养，形成了 11 种水解产物：H-Glu-His-Pro-NH2、H-Glu-His-Pro-OH、H-His-Pro-NH2、H-His-Pro-OH、His-Pro diketopiperazine、pGlu-His-Pro-OH、pGlu-His-OH、H-Glu-His-OH、H-Pro-His-OH、pGlu-OH 和 H-Glu-OH。结果表明，pGlu-His 连接和 pGlu 分子比 C 端羧酰胺对酸水解更敏感。随后，一种简单的解锁 pGlu 肽的方法被应用于 TRH。TRH 在 25°C 下于 70% 的甲磺酸（MSA）中水解，主要产物为 H-His-Pro-NH2 和 H-His-Pro-OH，次要产物为 H-Glu-His-Pro-NH2、二酮哌嗪和 pGlu-His-Pro-OH。在 25°C 条件下进行的 90% MSA 水解对 pGlu-His 键的裂解产物（H-His-Pro-NH2）具有高度选择性，而不会产生开环产物（H-Glu-His-Pro-NH2 和 H-Glu-His-Pro-OH）。3 天后，脱酰胺产物（H-His-Pro-OH 和 pGlu-His-Pro-OH）的产量低于 3%。

  DOI：

  10.1248/cpb.45.194

文献信息

• Selective labelling of peptides using (dienyl) iron tricarbonyl cations
  作者：John A. Carver、Betty Fates、Leon A. P. Kane-Maguire

  DOI：10.1039/c39930000928

  日期：——

  Dienyl cations of the type [(η5-R·C6H6)Fe(CO)3]+1 are shown to be versatile electrophilic reagents for the rapid and selective labelling of peptides and proteins, with the affinity for amino acid residues decreasing markedly in the order: cys (SH) > his (–N) > glu (δ-CO2–)≫α-NH2, lys (ε-NH2), ser (γ-OH), asn (-CONH)

  研究表明，[(η5-R-C6H6)Fe(CO)3]+1 型二烯丙基阳离子是一种多功能亲电试剂，可快速、选择性地标记肽和蛋白质，其对氨基酸残基的亲和力按以下顺序明显降低：cys (SH) > his (-N) > glu (δ-CO2-)≫α-NH2, lys (δµ-NH2), ser (γ-OH), asn (-CONH)
• Method of improving growth of poultry
  申请人：Pfizer Limited

  公开号：EP0080854A1

  公开（公告）日：1983-06-08

  A method of improving the efficiency of feed utilisation and/or growth of poultry comprises orally administering thyrotropin releasing hormone (TRH). The invention also provides poultry feed compositions containing TRH.

  提高家禽饲料利用率和/或生长效率的方法包括口服促甲状腺激素释放激素（TRH）。 本发明还提供了含有 TRH 的家禽饲料组合物。
• US4059692A
  申请人：——

  公开号：US4059692A

  公开（公告）日：1977-11-22
• Pressure/Temperature Combined Treatments of Precursors Yield Hormone-like Peptides with Pyroglutamate at the N Terminus
  作者：Avelina Fernández García、Peter Butz、Bernhard Trierweiler、Heike Zöller、Joachim Stärke、Eberhard Pfaff、Bernhard Tauscher

  DOI：10.1021/jf0348471

  日期：2003.12.1

  Peptides containing the cyclic product of glutamine at the N terminus are usually biologically active. If the cyclization of glutamine was associated with a volume reduction, pressure should displace the equilibrium in the direction of the lower volume. Here, results in model solutions and in whey are discussed, showing that the theorized cyclization of glutamine in Gln-His-ProNH(2) or Gln-Leu-ProNH(2) is significantly accelerated during the application of heat and even more strongly when elevated temperature and pressure combinations are used. The reaction rate depended on the intensity of the pressure treatment, the pH, and the nature of the amino acids adjacent to glutamine. The products of the reaction were identified as thyrotropin-releasing hormone (TRH) and [Leu(2)]TRH. The reported reactions could affect the naturally balanced concentration of short-chain peptides in foods and therefore induce unpredictable biological effects.
• Hydrolytic Cleavage of Pyroglutamyl-Peptide Bond. IV. Highly Selective Cleavage of Thyrotropin Releasing Hormone (TRH) in Aqueous Methanesulfonic Acid.
  作者：Kazuhiro OHKI、Naoki SAKURA、Tadashi HASHIMOTO

  DOI：10.1248/cpb.45.194

  日期：——

  The acid hydrolysis of thyrotropin releasing hormone (TRH) (pGlu-His-Pro-NH2) in various acids under several conditions and the highly selective cleavage of the pGlu-His bond are described. First, the decomposition of TRH in dilute acid was studied. The incubation of TRH in 1 N HCl at 60°C resulted in the formation of eleven hydrolysates, H-Glu-His-Pro-NH2, H-Glu-His-Pro-OH, H-His-Pro-NH2, H-His-Pro-OH, His-Pro diketopiperazine, pGlu-His-Pro-OH, pGlu-His-OH, H-Glu-His-OH, H-Pro-His-OH, pGlu-OH and H-Glu-OH. The results showed that the pGlu-His linkage and pGlu moiety were more sensitive than the C-terminal carboxamide to the acid hydrolysis. Then, a simple means of deblocking pGlu-peptide was applied to TRH. The hydrolysis of TRH in 70% methanesulfonic acid (MSA) at 25°C produced H-His-Pro-NH2 and H-His-Pro-OH as major products, and H-Glu-His-Pro-NH2, the diketopiperazine and pGlu-His-Pro-OH as minor products. The 90% MSA hydrolysis at 25°C was highly selective for the cleavage product (H-His-Pro-NH2) of the pGlu-His bond, without affording the ring-opened products (H-Glu-His-Pro-NH2 and H-Glu-His-Pro-OH). The yield of deamidated products (H-His-Pro-OH and pGlu-His-Pro-OH) was less than 3% after 3 d.

  本文描述了促甲状腺激素释放激素（TRH）（pGlu-His-Pro-NH2）在多种条件下在各种酸中的酸水解以及 pGlu-His 键的高选择性裂解。首先，研究了 TRH 在稀酸中的分解。将 TRH 在 60°C 的 1 N HCl 中培养，形成了 11 种水解产物：H-Glu-His-Pro-NH2、H-Glu-His-Pro-OH、H-His-Pro-NH2、H-His-Pro-OH、His-Pro diketopiperazine、pGlu-His-Pro-OH、pGlu-His-OH、H-Glu-His-OH、H-Pro-His-OH、pGlu-OH 和 H-Glu-OH。结果表明，pGlu-His 连接和 pGlu 分子比 C 端羧酰胺对酸水解更敏感。随后，一种简单的解锁 pGlu 肽的方法被应用于 TRH。TRH 在 25°C 下于 70% 的甲磺酸（MSA）中水解，主要产物为 H-His-Pro-NH2 和 H-His-Pro-OH，次要产物为 H-Glu-His-Pro-NH2、二酮哌嗪和 pGlu-His-Pro-OH。在 25°C 条件下进行的 90% MSA 水解对 pGlu-His 键的裂解产物（H-His-Pro-NH2）具有高度选择性，而不会产生开环产物（H-Glu-His-Pro-NH2 和 H-Glu-His-Pro-OH）。3 天后，脱酰胺产物（H-His-Pro-OH 和 pGlu-His-Pro-OH）的产量低于 3%。