L-蛋氨酰甘氨酰甘氨酸 | 14486-02-3

• 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-蛋氨酰甘氨酰甘氨酸
• 英文名称: Met-Gly-Gly
• 英文别名: H-Met-gly-gly-OH；2-[[2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]acetyl]amino]acetic acid
• CAS: 14486-02-3
• 化学式: C₉H₁₇N₃O₄S
• mdl: MFCD00190956
• 分子量: 263.318
• InChiKey: UZWMJZSOXGOVIN-LURJTMIESA-N

物化性质

• 熔点：
  208-209 °C (decomp)
• 沸点：
  649.4±55.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-蛋氨酰甘氨酰甘氨酸 以 水 为溶剂， 生成
  参考文献：
  名称：

  ˙OH自由基诱导含蛋氨酸的肽脱羧。肽序列和净电荷的影响

  摘要：

  ˙OH自由基诱导的含蛋氨酸肽的氧化会导致蛋氨酸单元位置相对于末端功能（Met–Gly，Met–Glu，Met–Gly–Gly，Gly–Met -Gly，Gly-Met和Gly-Gly-Met），或具有位于蛋氨酸N-末端的相邻氨基酸（Ala-Met，β-Ala-Met，Val-Met，Leu-Met，Ser -Met，Thr-Met，His-Met，γ-Glu-Met，Pro-Met，Gly-Gly-Phe-Met和Tyr-Gly-Gly-Phe-Met）。γ-射线分解测得的CO 2产率从0％（Met–Gly，Met–Glu，Met–Gly–Gly，Gly–Met–Gly和Pro–Met）变化到约80％（γ–Glu–Met）可用的˙OH自由基。从机理上讲，脱羧被认为是通过分子内“外层”电子从甲硫氨酸羧酸盐官能团转移到氧化硫官能团S˙ +。γ-Glu-Met中存在一条额外的N末端脱羧途径，该途

  DOI：

  10.1039/p29910000353
• 作为产物：
  描述：

  benzyl (S)-(1-hydrazinyl-4-(methylthio)-1-oxobutan-2-yl)carbamate 在 盐酸 、 甲醇 、 sodium hydroxide 、 钯 、 溶剂黄146 、 sodium nitrite 作用下， 生成 L-蛋氨酰甘氨酰甘氨酸
  参考文献：
  名称：

  Dekker; Taylor; Fruton, Journal of Biological Chemistry, 1949, vol. 180, p. 155,157

  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。
• Siebert, Andreas F. M.; Sheldrick, William S., Journal of the Chemical Society, Dalton Transactions, 1997, p. 385 - 394
  作者：Siebert, Andreas F. M.、Sheldrick, William S.

  DOI：——

  日期：——
• 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.
• Mechanism of 4-carboxybenzophenone-sensitized photooxidation of methionine-containing dipeptides and tripeptides in aqueous solution
  作者：Bronislaw Marciniak、Gordon L. Hug、Krzysztof Bobrowski、Halina Kozubek

  DOI：10.1021/j100036a037

  日期：1995.9

  The mechanism of 4-carboxybenzophenone (CB)-sensitized photooxidation of methionine-containing dipeptides (Met-Gly and Gly-Met) and tripeptides (Met-Gly-Gly, Gly-Met-Gly, and Gly-Gly-Met) was investigated using nanosecond flash photolysis and steady-state photolysis. The rate constants for quenching of the CB triplet by sulfur-containing peptides were determined to be in the range (1.8-2.3) x 10(9) M(-1) s-(1) for neutral and alkaline solutions. The presence of the various electron-transfer intermediates accompanying the CB triplet quenching events was identified through the use of a multiple-regression procedure that was used to resolve the experimental transient spectra into components. The intermediates identified were the CB ketyl radical anion, the CB ketyl radical, intermolecularly (S therefore S)-bonded radical cations, and intramolecularly (S therefore N)-bonded radical cations derived from peptides. The spectra of appropriate (S therefore S)(+) and (S therefore N)(+) intermediates for the peptides were determined from complementary pulse radiolysis studies in acidified aqueous solutions of the peptides. The types of intermediates were found to depend on the pH of the solution and on the location of the methionine unit with respect to the terminal functions. The quantum yields of all the transients and the kinetics of their formation and decay were measured by flash photolysis, and quantum yields of CO2 formation were measured by steady-state photolysis. These results were based on the resolution of the spectral components in the transient absorption spectra at various delays after the flash. A detailed mechanism of the CB-sensitized photooxidation of methionine-containing peptides was discussed and compared to that for methionine.
• Dekker; Taylor; Fruton, Journal of Biological Chemistry, 1949, vol. 180, p. 155,157
  作者：Dekker、Taylor、Fruton

  DOI：——

  日期：——