L-亮氨酰-甘氨酰-氨基乙酸 | 2576-67-2

• 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-亮氨酰-甘氨酰-氨基乙酸
• 英文名称: [(S)-2-(2-Amino-acetylamino)-4-methyl-pentanoylamino]-acetic acid
• 英文别名: Gly-Leu-Gly；GlyLeuGly；glycyl=>L-leucyl=>-glycine；Glycyl=>L-leucyl=>-glycin；Glycyl=>L-leucyl=>glycin; N-(N-Glycyl-L-leucyl)-glycin；[L-2-(Aminoacetyl-amino)-4-methyl-valerylamino]-essigsaeure；2-[[(2S)-2-[(2-azaniumylacetyl)amino]-4-methylpentanoyl]amino]acetate
• CAS: 2576-67-2
• 化学式: C₁₀H₁₉N₃O₄
• mdl: MFCD00037776
• 分子量: 245.279
• InChiKey: CCBIBMKQNXHNIN-ZETCQYMHSA-N

物化性质

• 沸点：
  573.7±45.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-亮氨酰-甘氨酰-氨基乙酸 在 sodium hydroxide 、 钯 、 溶剂黄146 作用下， 生成 glycyl=>glycyl=>L-leucyl=>glycine ; diglycyl-L-leucyl-glycine
  参考文献：
  名称：

  Bergmann; Zervas; Fruton, Journal of Biological Chemistry, 1935, vol. 111, p. 225,243

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-(2-amino-4-methylpentanamido)acetate 在 sodium hydroxide 、 碳酸氢钠 、 乙酸乙酯 作用下， 生成 L-亮氨酰-甘氨酰-氨基乙酸
  参考文献：
  名称：

  Bergmann; Zervas; Fruton, Journal of Biological Chemistry, 1935, vol. 111, p. 225,243

  摘要：

  DOI：

文献信息

• Thermodynamic properties of peptide solutions. Part 6.—The amino acid side-chain contributions to the partial molar volumes and heat capacities of some tripeptides in aqueous solution
  作者：Julia F. Reading、Gavin R. Hedwig

  DOI：10.1039/ft9908603117

  日期：——

  molar volumes, V02, and partial molar heat capacities, C0p, 2, have been determined for the tripeptides glycyl-L-valylglycine, glycyl-DL-serylglycine and the D and L isomers of glycylleucylglycine in aqueous solution at 298.15 K. These V02 and C0p, 2 results, in conjunction with those for glycylglycylglycine, were used to estimate the contribution of the side chains to the thermodynamic properties. The

  已经确定了三肽甘油基-L-戊基甘氨酸，甘油基-DL-丝氨基甘氨酸以及水溶液中glycylleucylglycine的D和L异构体的极限偏摩尔体积V 0 2和偏摩尔热容C 0 p，2 298.15K。将这些V 0 2和C 0 p，2结果与甘氨酰甘氨酰甘氨酸的结果一起用于估算侧链对热力学性质的贡献。将获得的结果与使用V 0估计的结果进行比较2和C 0 p，2个氨基酸和二肽数据。比较表明，序列甘氨酰-X-甘氨酸的三肽是合理的模型，用于估计溶剂可及的侧链对蛋白质的热力学性质的贡献。
• 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。
• New Amine-masking Groups for Peptide Synthesis
  作者：Frank C. McKay、Noel F. Albertson

  DOI：10.1021/ja01574a029

  日期：1957.9
• Simmonds et al., Journal of Biological Chemistry, 1951, vol. 188, p. 251,260
  作者：Simmonds et al.

  DOI：——

  日期：——
• Moir, Michael E.; Crawford, Robert J., Canadian Journal of Chemistry, 1988, vol. 66, p. 2903 - 2913
  作者：Moir, Michael E.、Crawford, Robert J.

  DOI：——

  日期：——