γ-谷氨酰苯丙氨酸 | 7432-24-8

• 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: γ-谷氨酰苯丙氨酸
• 英文名称: L-g-Glutamyl-L-phenylalanine
• 英文别名: (S)-2-amino-5-((S)-1-carboxy-2-phenylethylamino)-5-oxopentanoic acid；γ-L-glutamyl-L-phenylalanine；L-γ-glutamyl-L-phenylalanine；N-γ-glutamylphenylalanine；gamma-L-glutamyl-L-phenylalanine；γ-glutamyl phenylalanine；gamma-Glutamylphenylalanine；(2S)-2-amino-5-[[(1S)-1-carboxy-2-phenylethyl]amino]-5-oxopentanoic acid
• CAS: 7432-24-8
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: XHHOHZPNYFQJKL-QWRGUYRKSA-N

物化性质

• 熔点：
  194-197 °C
• 沸点：
  622.0±55.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（少许）、甲醇（少许）、水（少许）
• 物理描述：
  Solid
• 碰撞截面：
  168.2 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 储存条件：
  -20°C

制备方法与用途

生物活性

γ-Glu-Phe（γ-谷氨酰苯丙氨酸）是由解淀粉芽孢杆菌 (GBA) 和米曲霉 (GAO) 合成的。γ-Glu-Phe 或其酶后反应混合物可增强商业酱油和模型鸡汤的鲜味强度。

靶点

Human Endogenous Metabolite

体外研究

γ-Glu-Phe、γ-Glu-Met 和 γ-Glu-Val 在通过液相色谱-串联质谱 (LC-MS/MS) MRM 模式检测时被识别于发酵面团中。与化学酸化对照相比，在含有 L. reuteri 的发酵面团中发现 γ-谷氨酰二肽的浓度更高，这表明蛋白酶解是生成 γ-谷氨酰二肽的重要因素。感官评价显示，γ-谷氨酰二肽含量较高的发酵面团相较于普通面包和传统发酵面团，在味道强度方面表现更优。使用 L. reuteri LTH5448 和 100-23 发酵的面团在咸味强度上存在差异，这种差异与 γ-谷氨酰二肽的不同浓度相关。

参考质量标准

外观：白色粉末 纯度 (HPLC) ≥98.0% 醋酸根含量 ≤12.0% 水分含量 ≤8.0% 肽含量 ≥80.0% 内毒素 ≤50EU/mg 氨基酸组成分析 ≤±10%

反应信息

• 作为反应物：
  描述：

  γ-谷氨酰苯丙氨酸 在 L-glutaminase from Bacillus amyloliquefaciens 作用下， 以 水 为溶剂， 反应 1.0h， 生成 γ-Glu-γ-Glu-γ-Glu-γ-Glu-γ-Glu-Phe
  参考文献：
  名称：

  Synthesis and Sensory Characteristics of Kokumi γ-[Glu]_n-Phe in the Presence of Glutamine and Phenylalanine: Glutaminase from Bacillus amyloliquefaciens or Aspergillus oryzae as the Catalyst

  摘要：

  The transpeptidase activity of glutaminase from Bacillus amyloliquefaciens (GBA) and Aspergillus oiyzae (GAO) to yield gamma-[Glu](n)-Phe peptides were verified for the first time. In the presence of Gin and Phe, gamma-Glu-Phe and gamma-Glu-gamma-Glu-Phe were synthesized by GAO, and gamma-Glu-Phe, gamma-Glu-gamma-Glu-Phe, gamma-Glu-gamma-Glu-gamma-Glu-Phe, gamma-Glu-gamma-Glu-gamma-Glu-gamma-Glu-Phe, and gamma-Glu-gamma-Glu-gamma-Glu-gamma-Glu-gamma-Glu-Phe were synthesized by GBA. The K-m values for the transpeptidation catalyzed by GBA and GAO were 47.88 and 153.92 mM (Phe as the acceptor), 84.89 and 236.47 mM (gamma-Glu-Phe as the acceptor), indicating that GBA had a greater affinity than GAO for Phe and gamma-Glu-Phe in the transpeptidation reaction. The K-m values for the transpeptidation catalyzed by GBA against acceptors, Phe and gamma-[Glu]((1 <= n<5))-Phe (47.88-206.47 mM), increased with an elevated number of gamma-glutamyl residue within the acceptor. The optimal conditions for gamma-[Glu](n)-Phe synthesis were pH 10 and 37 degrees C for 3 h, 300 mM Gln, 100 mM Phe, 0.05 U/mL GBA. All the gamma-[Glu]((1 <= n<5))-Phe exhibited astringency in water and imparted a kokumi taste to commercial soy sauce and model chicken broth. The astringent threshold values (2.5-3.92 mM) were approximately 3-fold of the kokumi threshold concentrations (0.78-1.53 mM). gamma-[Glu](n)-Phe or the post-enzymatic reaction mixture enhanced the umami intensity of commercial soy sauce and model chicken broth.

  DOI：

  10.1021/acs.jafc.7b03419
• 作为产物：
  描述：

  N-[(1,1-二甲基乙氧基)羰基]-L-谷氨酸 1-乙基酯 在 甲醇 、 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 γ-谷氨酰苯丙氨酸
  参考文献：
  名称：

  γ-Glutamyl-dipeptides: Easy tools to rapidly probe the stereoelectronic properties of the ionotropic glutamate receptor binding pocket

  摘要：

  gamma-Glutamyl-dipeptides, built by condensing the distal carboxylate of L-Glu (or D-Glu) onto a series of differently functionalized amino acids, were prepared and used as tools for rapidly probing the stereo electronic properties of iGluRs, searching for subtype-selective ligands. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.11.025

文献信息

• Molecular Cloning and Characterization of γ-Glutamyltranspeptidase from<i>Pseudomonas nitroreducens</i>IFO12694
  作者：Masashi IMAOKA、Shigekazu YANO、Masashi OKUMURA、Takao HIBI、Mamoru WAKAYAMA

  DOI：10.1271/bbb.100199

  日期：2010.9.23

  γ-Glutamyltranspeptidase from Pseudomonas nitroreducens IFO12694 (PnGGT) exhibited higher hydrolytic activity than transfer activity, as compared with other γ-glutamyltranspeptidases (GGTs). PnGGT showed little activity towards most of l-amino acids and towards glycyl-glycine, which is often used as a standard γ-glutamyl accepter in GGT transfer reactions. The preferred substrates for PnGGT as a γ-glutamyl accepter were amines such as methylamine, ethylamine, and isopropylamine.

  与其它γ-谷氨酰转肽酶（GGT）相比，来自IFO12694的铜绿假单胞菌（PnGGT）展现出更高的水解活性而非转移活性。PnGGT对大多数L-氨基酸和常在GGT转移反应中用作标准γ-谷氨酰受体的甘氨酰甘氨酸表现出极低活性。作为γ-谷氨酰受体，PnGGT的优先底物为甲胺、乙胺和异丙胺等胺类。
• BETA-HAIRPIN PEPTIDOMIMETICS AS SELECTIVE ELASTASE INHIBITORS
  申请人：POLYPHOR AG

  公开号：US20160333053A1

  公开（公告）日：2016-11-17

  β-Hairpin peptidomimetics of the general formula cyclo(-Xaa 1 -Xaa 2 -Thr 3 -Xaa 4 -Ser 5 -Xaa 6 -Xaa 7 -Xaa 8 -Xaa 9 -Xaa 10 -Xaa 11 -Xaa 12 -Xaa 13 -) and pharmaceutically acceptable salts thereof, with Xaa 1 , Xaa 2 , Xaa 4 , Xaa 6 , Xaa 7 , Xaa 8 , Xaa 9 , Xaa 10 , Xaa 11 , Xaa 12 and Xaa 13 being amino acid residues of certain types which are defined in the description and the claims, have elastase inhibitory properties, especially against human neutrophil elastase, and can be used for preventing infections or diseases related to such infections in healthy individuals or for slowing infections in infected patients. The compounds of the invention can further be used where cancer, or immunological diseases, or pulmonary diseases, or cardiovascular diseases, or neurodegenerative diseases, or inflammation, or diseases related to inflammation, are mediated or resulting from elastase activity. These peptidomimetics can be manufactured by a process which is based on a mixed solid- and solution phase synthetic strategy.

  β-头发环肽类似物的一般公式为cyclo(-Xaa1-Xaa2-Thr3-Xaa4-Ser5-Xaa6-Xaa7-Xaa8-Xaa9-Xaa10-Xaa11-Xaa12-Xaa13-)及其药学上可接受的盐，其中Xaa1、Xaa2、Xaa4、Xaa6、Xaa7、Xaa8、Xaa9、Xaa10、Xaa11、Xaa12和Xaa13是在描述和权利要求中定义的某些类型的氨基酸残基，具有弹性酶抑制性质，特别是对人类中性粒细胞弹性蛋白酶，可用于预防健康个体中与此类感染相关的感染或疾病，或者用于减缓感染患者中的感染。该发明的化合物还可用于癌症、免疫性疾病、肺部疾病、心血管疾病、神经退行性疾病、炎症或与炎症相关的疾病由弹性酶活性介导或由此导致的情况。这些肽类似物可以通过基于混合固相和溶液相合成策略的过程制造。
• Enzymatic Synthesis of γ‐Glutamyl Dipeptides Catalysed by Mutant <i>E. coli</i> γ‐Glutamyltransferases
  作者：Marco Rabuffetti、Giovanna Speranza、Cinzia Calvio、Carlo F. Morelli

  DOI：10.1002/ejoc.202200907

  日期：2022.11.18

  identified inside the active site of E. coli γ-glutamyltransferase, putatively involved in acceptor substrate binding. Point-mutation of these residues afforded two mutant enzymes with altered catalytic properties. Mutant T413L showed a very promising transpeptidation-to-hydrolysis ratio up to 20 : 1. The two mutants were tested as biocatalysts for the enzymatic synthesis of γ-glutamyl dipeptides with flavor-enhancer

  在大肠杆菌γ-谷氨酰转移酶的活性位点内鉴定出两个残基，推测与受体底物结合有关。这些残基的点突变提供了两种催化特性改变的突变酶。突变体 T413L 显示出非常有希望的高达 20:1 的转肽水解比。这两个突变体被测试为用于酶促合成具有增味特性的 γ-谷氨酰二肽的生物催化剂。
• Reagents for assay of gamma-glutamyl-transpeptidase
  申请人：UNITIKA LTD.

  公开号：EP0266905A1

  公开（公告）日：1988-05-11

  A reagent for assaying γ-glutamyltranspeptidase (γ-GTP) which contains an amino acid dehydrogenase and a substrate specific to γ-glutamyltranspeptidase activity. The reagent can be used to assay the γ-GTP activity directly from the continuous course of reaction without using a standard substance with known activity. The procedure required is simple and easy, and the reagent is capable of determining γ-GTP activity with good accuracy and without affecting by interfering substances, making it satisfactory for routine use in clinical laboratories.

  一种用于测定γ-谷氨酰转肽酶（γ-GTP）的试剂，它含有氨基酸脱氢酶和对γ-谷氨酰转肽酶活性有特异性的底物。该试剂无需使用已知活性的标准物质，即可直接从连续反应过程中检测 γ-GTP 活性。该试剂所需的步骤简单易行，能够准确测定 γ-GTP 活性，且不受干扰物质的影响，因此非常适合临床实验室的常规使用。
• Biomarkers for fatty liver disease and methods using the same
  申请人：Metabolon Inc.

  公开号：EP2546649A2

  公开（公告）日：2013-01-16

  The present invention provides various biomarkers of fatty liver disease, including steatosis and steatohepatitis. The present invention also provides various methods of using the biomarkers, including methods for diagnosis of fatty liver disease, methods of determining predisposition to fatty liver disease, methods of monitoring progression/regression of fatty liver disease, methods of assessing efficacy of compositions for treating fatty liver disease, methods of screening compositions for activity in modulating biomarkers of fatty liver disease, methods of treating fatty liver disease, as well as other methods based on biomarkers of fatty liver disease.

  本发明提供了脂肪肝的各种生物标志物，包括脂肪变性和脂肪性肝炎。本发明还提供了使用这些生物标志物的各种方法，包括诊断脂肪肝的方法、确定脂肪肝易感性的方法、监测脂肪肝进展/恶化的方法、评估治疗脂肪肝组合物疗效的方法、筛选组合物调节脂肪肝生物标志物活性的方法、治疗脂肪肝的方法以及基于脂肪肝生物标志物的其他方法。

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