L-酪氨酰甘氨酰甘氨酸 | 21778-69-8

• 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: L-酪氨酰甘氨酰甘氨酸
• 英文名称: tyrosylglycylglycine
• 英文别名: Tyr-Gly-Gly；YGG zwitterion；2-[[2-[[(2S)-2-azaniumyl-3-(4-hydroxyphenyl)propanoyl]amino]acetyl]amino]acetate
• CAS: 21778-69-8
• 化学式: C₁₃H₁₇N₃O₅
• mdl: MFCD00037786
• 分子量: 295.295
• InChiKey: HIINQLBHPIQYHN-JTQLQIEISA-N

物化性质

• 熔点：
  193-195℃
• 沸点：
  741.8±60.0 °C(Predicted)
• 密度：
  1.381

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  L-酪氨酰甘氨酰甘氨酸 在 sodium hydroxide 、 methylcaprylammoniumchloride 、 p-nitrobenzophenone oxime resin 、 溶剂黄146 、 magnesium monoperoxyphthalate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 水 为溶剂， 反应 18.17h， 生成 N-carbobenzyloxy-O-carbobenzyloxy-L-tyrosylglycylglycyl-L-phenylalanine 4-(methylsulfonyl)phenyl ester
  参考文献：
  名称：

  Selective catalysis of ester aminolysis: an approach to peptide active esters

  摘要：

  DOI：

  10.1021/jo00298a024
• 作为产物：
  描述：

  O-acetyl-N-benzyloxycarbonyl L-tyrosine 在 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 二辛基甲胺 、 五氯化磷 作用下， 生成 L-酪氨酰甘氨酰甘氨酸
  参考文献：
  名称：

  679.由脱水N-羧基氨基酸合成简单的肽

  摘要：

  DOI：

  10.1039/jr9500003461

文献信息

• Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids
  作者：Shinya Furukawa、Takahide Fukuyama、Akihiro Matsui、Mai Kuratsu、Ryotaro Nakaya、Takashi Ineyama、Hiroshi Ueda、Ilhyong Ryu

  DOI：10.1002/chem.201501783

  日期：2015.8.17

  method for the synthesis of dipeptides has been developed, which does not require any coupling reagents. This method is based on the reaction of readily available HCl salts of amino acid methyl esters with tetrabutylphosphonium amino acid ionic liquids. The isolation procedure of stepwise treatment with AcOH is easy to carry out. The method was extended to the synthesis of tripeptide, tyrosyl‐glycyl‐glycine

  已经开发了合成二肽的通用方法，该方法不需要任何偶联剂。该方法基于容易获得的氨基酸甲酯的HCl盐与四丁基phosph氨基酸离子液体的反应。用AcOH逐步处理的分离过程很容易进行。该方法还扩展到IMREG-1中也存在的三肽酪氨酰甘氨酰甘氨酸的合成。
• Inhibition of iodine-125 labeled ristocetin binding to Micrococcus luteus cells by the peptides related to bacterial cell wall mucopeptide precursors: quantitative structure-activity relationships
  作者：Ki-Hwan Kim、Yvonne Martin、Ellen Otis、James Mao

  DOI：10.1021/jm00121a018

  日期：1989.1

  Quantitative structure-activity relationships (QSAR) of N-Ac amino acids, N-Ac dipeptides, and N-Ac tripeptides in inhibition of 125I-labeled ristocetin binding to Micrococcus luteus cell wall have been developed to probe the details of the binding between ristocetin and N-acetylated peptides. The correlation equations indicate that (1) the binding is stronger for peptides in which the side chain of

  已开发了N-Ac氨基酸，N-Ac二肽和N-Ac三肽在抑制125I标记的瑞氏菌素与黄褐微球菌细胞壁结合中的定量构效关系（QSAR），以探索ristocetin之间的结合细节和N-乙酰化的肽 相关方程表明（1）对于C末端氨基酸侧链具有较大摩尔折射率（MR）值的肽，其结合作用更强；（2）对于极性肽，其结合作用较弱。 （3）N-Ac二肽中的N末端氨基酸对结合亲和力的贡献是C末端氨基酸的12倍，
• Transmucosal Delivery of Methionine Enkephalin. I: Solution Stability and Kinetics of Degradation in Various Rabbit Mucosa Extracts
  作者：In Koo Chun、Yie W. Chien

  DOI：10.1002/jps.2600820408

  日期：1993.4

  showed that Met-Enk is most stable at pH approximately 5.0. Various mucosae excised from rabbit were mounted on Valia-Chien permeation cells and exposed to isotonic phosphate buffer at physiologic pHs. Mucosal and serosal extracts were collected from the donor and receptor solutions, respectively. The degradation of Met-Enk in the extracts followed first-order kinetics, but no significant difference in

  为了评估蛋氨酸脑啡肽（Tyr-Gly-Gly-Phe-Met； Met-Enk）经粘膜递送的可行性，重要的是首先研究其理化和酶稳定性。通过高效液相色谱法在pH 2.01-9.84和37-45℃下测定Met-Enk在水溶液中的降解动力学。计算一级速率常数（k），log k-pH曲线表明，Met-Enk在pH约5.0时最稳定。将从兔切下的各种粘膜固定在Valia-Chien渗透细胞上，并在生理pH值下暴露于等渗磷酸盐缓冲液中。分别从供体和受体溶液中收集粘膜和浆膜提取物。提取物中Met-Enk的降解遵循一级动力学，但是，无论使用何种粘膜类型，粘膜和浆膜提取物的降解率均无显着差异。直肠粘膜提取物中降解最迅速，其次是阴道和鼻粘膜。主要代谢物是Des-Tyr-Met-Enk和酪氨酸（Tyr），表明氨基肽酶的酶促水解。但是，数据还表明，二肽基肽酶和二肽基羧肽酶可能在Met-Enk的降解中起一定作用。通过
• Real-time reaction monitoring by continuous-introduction ion-spray tandem mass spectrometry
  作者：Edgar D. Lee、Wolfgang Mueck、Jack D. Henion、Thomas R. Covey

  DOI：10.1021/ja00195a012

  日期：1989.6

  for real-time measurement of reactions. The reaction medium, reactants, and products were transferred to the ion source of the mass spectrometer from the reaction vessel in less than 1 s. A variety of model reactions have been investigated to demonstrate the feasibility acd potential for continuous-introduction ion-spray mass spectrometry for real-time reaction monitoring. The half-life for the solvolysis

  温度控制的反应容器与大气压电离、三重四极杆质谱仪上的离子喷雾 LC/MS 接口紧密耦合，用于研究在溶液中发生的反应的机械和动力学方面。自由进入反应容器和温度控制以及最小的样品消耗使连续引入离子喷雾质谱法成为实时测量反应的有用方法。反应介质、反应物和产物在不到 1 s 的时间内从反应容器转移到质谱仪的离子源。已经研究了各种模型反应，以证明连续引入离子喷雾质谱法用于实时反应监测的可行性和潜力。测定了硫酸甲氢烯醇酮在水性介质中的溶解半衰期和乳糖酶对 0-硝基苯基 PD-吡喃半乳糖苷的酶促水解的 Michaelis-Menten 常数。在线获得了α-胰凝乳蛋白酶和亮氨酸氨肽酶对强啡肽 1-8 的酶水解以及使用 fi-巯基乙醇对催产素中二硫键的还原，以强调该技术在肽测序和结构解析方面的能力。
• Linear energy correlations and failures in the low-energy tandem mass spectra of protonatedN-benzoylated tripeptides: Tools for probing mechanisms of CAD processes
  作者：Daniel G. Morgan、Maurice M. Bursey

  DOI：10.1002/jms.1190300410

  日期：1995.4

  The backbone cleavages for three series of protonated N-benzoyl tripeptide ions were studied in a hybrid tandem mass spectrometer: (i) benzoyl-Gly-Gly-Xxx, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Glu, Pro and Trp, (ii) benzoyl-Gly-Xxx-Gly, where Xxx = Gly, Ala, Leu, Phe, Tyr, Met and Trp, and (iii) benzoyl-Xxx-Gly-Gly, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Pro and Trp. C-Terminal y-type ions and N-terminal a- and b-type ions were noted in all three cases. For benzoyl-Gly-Gly-Xxx, a linear relationship between log (y1/b2) and the proton affinity of the C-terminal amino acid substituents was found: as the proton affinity of the C-terminal residue increases, the fraction of y1 ion formation increases. A similar relationship was noted for the benzoyl-Xxx-Gly-Gly tripeptides between log (y2/b1) and the proton affinity of the N-terminal amino acid substituent: as the proton affinity of the N-terminal residue increases, the fraction of b1 ion formation increases. For the series benzoyl-Gly-Xxx-Gly, these relationships did not hold true. These observations point to similar reaction pathways throughout the benzoyl-Gly-Gly-Xxx series and also similar pathways throughout the benzoyl-Xxx-Gly-Gly, but pathways that are substituent dependent for benzoyl-Gly-Xxx-Gly. The increased correlation coefficients for benzoyl-Gly-Gly-Xxx and benzoyl-Xxx-Gly-Gly when compared with the free tripeptides, suggest that fewer interfering competitive reactions exist, as fewer possibilities for internal hydrogen bonding exist in the N-benzoyl derivatives versus the free compounds.

  在一台混合串联质谱仪上，研究了三种系列的质子化N-苯甲酰三肽离子的骨架断裂：（i）苯甲酰-Gly-Gly-Xxx，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Glu、Pro和Trp，（ii）苯甲酰-Gly-Xxx-Gly，其中Xxx = Gly、Ala、Leu、Phe、Tyr、Met和Trp，以及（iii）苯甲酰-Xxx-Gly-Gly，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Pro和Trp。在所有三种情况下，都观察到了C端y型离子和N端a型及b型离子。对于苯甲酰-Gly-Gly-Xxx，发现log（y1/b2）与C端氨基酸取代基的质子亲和力之间存在线性关系：随着C端残基的质子亲和力增加，y1离子的形成分数增加。对于苯甲酰-Xxx-Gly-Gly三肽，log（y2/b1）与N端氨基酸取代基的质子亲和力之间存在类似的关系：随着N端残基的质子亲和力增加，b1离子的形成分数增加。对于苯甲酰-Gly-Xxx-Gly系列，这些关系并不成立。这些观察结果表明，在苯甲酰-Gly-Gly-Xxx系列和苯甲酰-Xxx-Gly-Gly系列中存在类似的反应途径，但对于苯甲酰-Gly-Xxx-Gly，途径依赖于取代基。与自由三肽相比，苯甲酰-Gly-Gly-Xxx和苯甲酰-Xxx-Gly-Gly的相关系数增加，表明存在的干扰竞争反应较少，因为在N-苯甲酰衍生物中内部氢键的可能性比自由化合物少。