H-Trp-Met-Asp-OH | 97586-87-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: H-Trp-Met-Asp-OH
• 英文别名: WMD；Trp-Met-Asp；(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]butanedioic acid
• CAS: 97586-87-3
• 化学式: C₂₀H₂₆N₄O₆S
• 分子量: 450.516
• InChiKey: NESIQDDPEFTWAH-BPUTZDHNSA-N

物化性质

• 沸点：
  842.8±65.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  200
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-苯丙氨酰胺 、 H-Trp-Met-Asp-OH 在 thermolysin 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以89%的产率得到四肽胃泌素
  参考文献：
  名称：

  Thermolysin-catalyzed synthesis of peptide amides.

  摘要：

  研究了热溶解酶在各种氨基酸酰胺和受保护或未受保护的肽之间的酶促缩合作用。作为模型，制备了三种受保护的四肽酰胺：Boc-Trp-Met-Asp-X、Boc-Ser-Glu-Ala-X 和 Boc-Ser-Lys-Ala-X，以及两种未受保护的四肽酰胺：H-Trp-Met-Asp-X 和 H-Phe-Met-Arg-X、X=Phe-NH2、Leu-NH2、Phe-NHEt、Val-NH2、Ala-NH2、（对氟）Phe-NH2]，并考察了各种实验条件（pH 值、溶剂和时间）的影响。此外，在热溶解酶的帮助下，通过添加上述各种酰胺，将氧化胰岛素 B 链的 C 端拉长为酰胺。

  DOI：

  10.1248/cpb.36.4345
• 作为产物：
  描述：

  四肽胃泌素 在 endoproteinase Glu-C 作用下， 以 水 为溶剂， 反应 2.0h， 生成 H-Trp-Met-Asp-OH
  参考文献：
  名称：

  Solid-state stability studies of cholecystokinin (CCK-4) peptide under nonisothermal conditions using thermal analysis, chromatography and mass spectrometry

  摘要：

  The solid-state stability of cholecystokinin (CCK-4) peptide under nonisothermal conditions was studied by differential scanning calorimetry (DSC), chromatography and mass spectrometry, identifying and schematizing the degradation products. To model the degradation mechanism of the peptide using the combined Kissinger and direct-differential methods, the observed degradation process was characterized by decomposition temperature (T-m), reacted fraction (alpha(m)), activation energy (E-a), and pre-exponential factor (A). Results obtained by the two calculation methods were similar.The cleavage reaction on both N- and C-terminal sides of aspartic acid was the principal degradation pathway, although the reaction can occur consecutively and/or in parallel. Therefore to determine the relative importance of the different degradation pathways, a system of differential equations relevant to each degradation reaction was analysed using the R(R) statistical program. The results obtained show that the consecutive reaction was the less plausible, whereas a slightly better fit was obtained for the reaction with both processes than for the in-parallel reaction. In this situation, the F-test was applied to discriminate between the models, indicating that the simpler model is the most probable. In conclusion, the results demonstrate for the first time that, in solid-state, n-1 cleavage occurs in parallel to n+1 cleavage at aspartic acid residues and not consecutively. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejps.2009.12.010