甘氨酰甘氨酰酪氨酸 | 17343-07-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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: 甘氨酰甘氨酰酪氨酸
• 英文名称: gly-gly-tyr
• 英文别名: glycylglycyl-L-tyrosine；NH2-Gly-Gly-Tyr-OH；H-Gly-Gly-Tyr-OH；TyrGlyGly；HGlyGlyTyrOH；(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• CAS: 17343-07-6
• 化学式: C₁₃H₁₇N₃O₅
• mdl: MFCD27977957
• 分子量: 295.295
• InChiKey: INLIXXRWNUKVCF-JTQLQIEISA-N

物化性质

• 熔点：
  >200°C (dec.)
• 沸点：
  720.2±60.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（稍微加热）、水（稍微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甘氨酰-L-酪氨酸	N-Gly-Tyr	658-79-7	C11H14N2O4	238.243
  ——	H-Tyr-Gly-Gly-Phe-Leu-NH2	80479-94-3	C28H37N5O7	555.631
  ——	Met-enkephalin	77658-98-1	C27H35N5O7S	573.67

反应信息

• 作为反应物：
  描述：

  甘氨酰甘氨酰酪氨酸 在 ammonium hydroxide 、 sodium hydroxide 作用下， 生成 N-[N-(N-L-alanyl-glycyl)-glycyl]-l-tyrosine
  参考文献：
  名称：

  Abderhalden et al., Fermentforschung, 1942, vol. 16, p. 98,114

  摘要：

  DOI：
• 作为产物：
  描述：

  甘氨酰-L-酪氨酸 在 sodium hydroxide 、 氨 作用下， 生成 甘氨酰甘氨酰酪氨酸
  参考文献：
  名称：

  Abderhalden et al., Fermentforschung, 1942, vol. 16, p. 98,114

  摘要：

  DOI：

文献信息

• 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。
• [EN] CYCLAM BASED COMPOUNDS, THEIR CONJUGATES, CO-ORDINATION COMPOUNDS, PHARMACEUTICAL COMPOSITION CONTAINING THEREOF, METHOD OF PREPARATION AND USE THEREOF<br/>[FR] COMPOSÉS À BASE DE CYCLAME, LEURS CONJUGUÉS, COMPOSÉS DE COORDINATION, COMPOSITION PHARMACEUTIQUE LES CONTENANT, PROCÉDÉ DE PRÉPARATION ET UTILISATION ASSOCIÉS
  申请人：UNIV KARLOVA

  公开号：WO2017084645A1

  公开（公告）日：2017-05-26

  Cyclam based compounds, their conjugates, co-ordination compounds, pharmaceutical composition containing thereof, method of preparation and use thereof The present invention relates to cyclam based compounds of the general formula (I), conjugates of such compounds with conjugation groups, their coordination compounds, targeting conjugates, method of preparation of cyclam based compounds, intermediate products for the preparation of cyclam based compounds, a pharmaceutical preparation containing them, and the use thereof.

  基于环戊胺的化合物、其共轭物、配位化合物、含有其的药物组合物、制备方法及使用方法。本发明涉及一般式(I)的基于环戊胺的化合物、这些化合物与共轭基的共轭物、它们的配位化合物、靶向共轭物、基于环戊胺的化合物的制备方法、制备基于环戊胺的化合物的中间产物、含有它们的药物制剂及其用途。
• The use of crown ethers in peptide chemistry IV. Solid phase synthesis of peptides using peptide fragments Nα protected with 18-crown-6
  作者：Paolo Botti、Haydn L. Ball、Emanuele Rizzi、Pierluigi Lucietto、Massimo Pinori、Paolo Mascagni

  DOI：10.1016/0040-4020(95)00206-n

  日期：1995.5

  The conditions under which peptide synthesis by the fragment condensation approach in the solid phase can be carried out using crown ethers as non-covalent protecting groups for the Nα amino group of peptides were determined. The dipeptide Gly-Gly was complexed with 18-crown-6 to establish the feasibilty of this new protection scheme and to optimise the reaction conditions. Nearly quantitative incorporation

  确定了可以使用冠醚作为肽的Nα氨基的非共价保护基通过固相中的片段缩合方法合成肽的条件。将二肽Gly-Gly与18-crown-6复合以建立这种新保护方案的可行性并优化反应条件。使用DCM作为活化和偶联反应溶剂，可以将络合物几乎定量地掺入到具有脯氨酸或Nα-烷基化氨基酸的树脂结合氨基酸上。由于除去冠醚保护剂，发现使用DMF作为溶剂和与树脂结合的伯氨基酸不利于反应产率。延长肽片段的长度以模拟在侧链上不具有任何反应性功能的五肽复合物，在与树脂结合的氨基酸和短肽的偶联反应中，得到的定量掺入量基本上是定量的。冠状分子提供的保护作用具有非共价特性，可通过用1％DIEA溶液进行快速处理将其从树脂结合的复合物中轻度去除。因此，链条组装的继续是可能的。获得的结果作为将非共价保护的概念扩展到含有Lys和Arg的肽的侧链的基础。冠状分子提供的保护作用具有非共价特性，可通过用1％DIEA溶液进行快速处理将其从树脂
• Improved Conjugation, 64-Cu Radiolabeling, in Vivo Stability, and Imaging Using Nonprotected Bifunctional Macrocyclic Ligands: Bis(Phosphinate) Cyclam (BPC) Chelators
  作者：Tomáš David、Veronika Hlinová、Vojtěch Kubíček、Ralf Bergmann、Franziska Striese、Nicole Berndt、Dávid Szöllősi、Tibor Kovács、Domokos Máthé、Michael Bachmann、Hans-Jürgen Pietzsch、Petr Hermann

  DOI：10.1021/acs.jmedchem.8b00932

  日期：2018.10.11

  ∼7.5–8.5 and ∼10–11, respectively) due to lower basicity. The Cu-64 labeling was efficient at room temperature (specific activity ∼100 GBq/μmol; 25 °C, pH 6.2, ∼100 ligand equiv, 10 min). A representative Cu-64-BPC was tested in vivo showing fast clearance and no nonspecific radioactivity deposition. The monoclonal anti-PSCA antibody 7F5 conjugates with thiocyanate BPC derivative or NODAGA were radiolabeled

  合成了在BP侧链上带有羧酸盐，胺，异硫氰酸盐，叠氮化物或环辛炔的带有双（次膦酸酯）的Cyclam（BPC）螯合剂的双功能衍生物。共轭不需要亚膦酸酯或环仲胺基的保护。在pH <〜8时，环胺不具有反应性（质子保护）。对于异硫氰酸酯偶联，寡肽N末端α-胺比烷基胺（例如Lysω-胺（p K a由于碱度较低，分别约为7.5至8.5和10至11）。Cu-64标记在室温下是有效的（比活〜100 GBq /μmol; 25°C，pH 6.2，约100当量配体，10分钟）。代表性的Cu-64-BPC在体内进行了测试，显示出快速清除并且没有非特异性放射性沉积。用硫氰酸盐BPC衍生物或NODAGA对单克隆抗PSCA抗体7F5偶联物进行了放射性标记，并通过PET在携带PC3-PSCA肿瘤的小鼠中进行了研究。与Cu-64标记的NODAGA-抗体结合物不同，放射性标记的BPC结合物在前列腺肿瘤中积累，脱靶吸收率低。BPC螯合剂在Cu-64
• High-Performance Liquid Chromatographic Analysis of Pulmonary Metabolites of Leu- and Met-Enkephalins in Isolated Perfused Rat Lung
  作者：Peter A. Crooks、Jerzy W. Krechniak、Jack W. Olson、Mark N. Gillespie

  DOI：10.1002/jps.2600740923

  日期：1985.9

  A high-performance liquid radiochromatographic analytical system has been developed which allows the determination of [3H]Leuenkephalin, [3H]Met-enkephalin and their potential metabolites [3H]TyrGlyGlyPhe, [3H]TyrGlyGly, [3H]TyrGly and [3H]tyrosine. Using this procedure, the biotransformation of each of the above enkephalins after 20 min of recirculating transit through isolated perfused rat lungs resulted

  开发了一种高效液相色谱分析系统，该系统可以测定[3H]吕克脑啡肽，[3H]蛋氨酸和它们的潜在代谢产物[3H] TyrGlyGlyPhe，[3H] TyrGlyGly，[3H] TyrGly和[3H]酪氨酸。使用此程序，上述每种脑啡肽在经过离体的灌注大鼠肺的循环转运20分钟后的生物转化导致形成两种主要代谢产物：酪氨酸和TyrGlyGly。结果表明脑啡肽的重要代谢可能发生在肺循环中。