Gly-Ala-Gly | 16422-05-2

• 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
• 英文名称: Gly-Ala-Gly
• 英文别名: L-glycyl-L-alanyl-L-glycine；glycyl-L-alanylglycine；glycylalanylglycine；GAG；Gly-L-AlaGly-OH；Gly-L-Ala-Gly；H-Gly-Ala-Gly-OH；2-[[(2S)-2-[(2-aminoacetyl)amino]propanoyl]amino]acetic acid
• CAS: 16422-05-2；53298-65-0
• 化学式: C₇H₁₃N₃O₄
• mdl: MFCD00083689
• 分子量: 203.198
• InChiKey: UGVQELHRNUDMAA-BYPYZUCNSA-N

物化性质

• 沸点：
  604.6±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  甲醇 、 Gly-Ala-Gly 在 盐酸 、 乙酸酐 作用下， 反应 0.17h， 生成 glycyl-L-alanylglycine methyl ester
  参考文献：
  名称：

  肽骨架的气相去质子化氢和甲基侧链的三肽及其甲基酯

  摘要：

  六种三肽（GlyGlyGly，GlyAlaGly，AlaGlyAla，AlaAlaAla，AibAibAib和SarSarSar）及其甲酯的气相酸度是通过傅立叶变换离子回旋共振质谱仪和G3（MP2）分子中的质子转移反应获得的轨道理论计算。所有六个肽的GA均在321.0–323.7 kcal / mol的范围内。它们的去质子化产生[M – H] -发生在C端羧酸基团。三肽的酸性比氨基酸甘氨酸（Gly）和丙氨酸（Ala）高约10 kcal / mol。这与三肽结构中广泛的氢键相符。对于甲酯，去质子化发生在肽主链上。G3（MP2）计算表明，最受能量支持的去质子化位点是酰胺氮，通常优选中心酰胺。氮去质子化所需的能量比亚甲基碳处的去质子化少10–20 kcal / mol。仅三种甲酯（GlyGlyGly-OMe，GlyAlaGly-OMe和AlaAlaAla-OMe）通过电喷雾电离实验性去质子化。这些酯的实验GAs在336

  DOI：

  10.1021/jp3113528
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 钯 、 溶剂黄146 作用下， 生成 Gly-Ala-Gly
  参考文献：
  名称：

  Optical Rotation of Peptides. II. Glycine and Alanine Tripeptides¹

  摘要：

  DOI：

  10.1021/ja01151a513

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。
• Metal Complexes of Peptides. III. The Preparation and Properties of Diammine(oligopeptidato)cobalt(III) Complexes
  作者：Hiroshi Kawaguchi、Mari Ishii、Tomoharu Ama、Takaji Yasui

  DOI：10.1246/bcsj.55.3750

  日期：1982.12

  Complexes of the [Co(tripeptidato)(NH3)2] and NH4[Co(tetrapeptidato)(NH3)2] types (tripeptidato and tetrapeptidato denote the tri- and tetraanions of the coordinating peptides respectively) have been prepared and characterized by means of their electronic, 1H NMR, and circular dichroism (CD) spectral data. In the NH4[Co(tetrapeptidato) (NH3)2] complex, the pep tide coordinates to cobalt(III) as a quadridentate

  [Co(tripeptidato)(NH3)2] 和 NH4[Co(tetrapeptidato)(NH3)2] 类型的复合物（三肽和四肽分别表示配位肽的三阴离子和四阴离子）已被制备和表征它们的电子、1H NMR 和圆二色性 (CD) 光谱数据。在 NH4[Co(tetrapeptidato) (NH3)2] 复合物中，肽通过氨基和三个酰胺基团的氮与钴 (III) 作为四齿配体配位。已发现邻位 CD 光谱的可加性适用于一系列含有 L-丙氨酸和/或甘氨酸残基的三肽的复合物。这些三肽和四肽复合物在水中很容易发生水化反应，释放出氨分子。
• Thermodynamic properties of peptide solutions 3. Partial molar volumes and partial molar heat capacities of some tripeptides in aqueous solution
  作者：Gavin R. Hedwig

  DOI：10.1007/bf00650418

  日期：1988.4

  Partial molar volumes, V2o, and partial molar heat capacities, Cp,2o, of the tripeptides glycylglycylglycine, glycylglycylalanine, glycylalanylglycine and alanylglycylglycine have been determined in aqueous solution at 25°C. For the three alanyl-containing tripeptides, the data indicate that the tripeptide-water interaction is influenced by the side chain position within the molecule. The results have

  三肽甘氨酰甘氨酰甘氨酸、甘氨酰甘氨酰丙氨酸、甘氨酰丙氨酰甘氨酸和丙氨酰甘氨酰甘氨酸的偏摩尔体积 V2o 和偏摩尔热容 Cp,2o 已在 25°C 的水溶液中测定。对于三个含丙氨酰的三肽，数据表明三肽-水相互作用受分子内侧链位置的影响。结果已根据可能的溶质溶剂相互作用进行了合理化。V2o 和 Cp.2o 数据也已用于计算对 a-CH3 侧链这些特性的贡献。
• Manganese complexes of nitrogen-containing macrocyclic ligands effective
  申请人：G. D. Searle & Co.

  公开号：US05874421A1

  公开（公告）日：1999-02-23

  The present invention is directed to low molecular weight mimics of superoxide dismutase (SOD) represented by the formula: ##STR1## wherein R, R', R.sub.1, R'.sub.1, R.sub.2, R'.sub.2, R.sub.3, R'.sub.3, R.sub.4, R'.sub.4, R.sub.5, R'.sub.5, R.sub.6, R'.sub.6, R.sub.7, R'.sub.7, R.sub.8, R'.sub.8, R.sub.9, and R'.sub.9 and X, Y, Z and n are as defined herein, useful as therapeutic agents for inflammatory disease states and disorders, ischemic/reperfusion injury, stroke, atherosclerosis, hypertension and all other conditions of oxidant-induced tissue damage or injury.

  本发明涉及超氧化物歧化酶（SOD）的低分子量模拟物，其化学式为：##STR1## 其中，R、R'、R1、R'1、R2、R'2、R3、R'3、R4、R'4、R5、R'5、R6、R'6、R7、R'7、R8、R'8、R9 和 R'9，以及 X、Y、Z 和 n 的定义如本文所述，作为治疗炎症性疾病状态和障碍、缺血/再灌注损伤、中风、动脉粥样硬化、高血压和所有由氧化剂引起的组织损伤或损伤的治疗剂。
• The application of circular dichroism spectroscopy for the determination of metal ion speciation and coordination modes of peptide complexes
  作者：Katalin Ősz、Beáta Bóka、Katalin Várnagy、Imre Sóvágó、Tibor Kurtán、Sándor Antus

  DOI：10.1016/s0277-5387(02)01151-8

  日期：2002.9

  Copper(II) and nickel(II) complexes of the tripeptides containing methionyl residues (GlyGyMet, GlyMetGly, MetGlyGly, MetMetAla, MetGlyMet and MetMetMet) and palladium(II) complexes of GlyMet, MetGly, GlyMetGly and GlyGlyMet were studied by CD spectroscopic measurements. Complex formation reactions between copper(II), nickel(II) and tripeptides were very similar to each other, [MH-2L](-) being the major species in alkaline solutions. CD spectroscopy, however, was a very sensitive tool for the elucidation of small structural differences among peptide complexes, including the weak axial or equatorial coordinations of thioether residues. The significant differences in the spectral parameters of the species [CuL](+), [CuH-1L] and [CuH-2L](-) made it also possible to calculate the stability constants and metal ion speciation from CD measurements. (C) 2002 Elsevier Science Ltd. All rights reserved.