H-Tyr-Asp-Pro-Ala-Pro-OH

• 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: H-Tyr-Asp-Pro-Ala-Pro-OH
• 英文别名: (2S)-1-[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-carboxypropanoyl]pyrrolidine-2-carbonyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
• 化学式: C₂₆H₃₅N₅O₉
• 分子量: 561.592
• InChiKey: JDSDPMXKPTUZKG-HVRBKMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  220
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Fmoc-L-丙氨酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-天冬氨酸 beta-叔丁酯 、 Fmoc-O-叔丁基-L-酪氨酸 生成 H-Tyr-Asp-Pro-Ala-Pro-OH
  参考文献：
  名称：

  The C-Terminus Shortened Analogs of the Insect Peptide Oostatic Hormone with Accelerated Activity

  摘要：

  Shortened analogs 1a-1f of the oostatic hormone 1g with a decreased number or an omission of the C-terminal Pro residues were synthesized for investigation of their effect on oogenesis in the flesh fly Sarcophaga bullata Parker (Diptera). Peptides 1b-1g were prepared by solid-phase synthesis on polystyrene/divinylbenzene polymer with a 2-chlorotrityl linker using Fmoc/tBu strategy in dimethylformamide (DMF). Tetrapeptide Ia, devoid of all the carboxyterminal Pro residues, was prepared by stepwise procedure in DMF solution from HCl-H-Ala-OMe using Boc-Pro-OH, Z-Asp(OtBu)-OSu, and Boc-Tyr-OSu. In general, the peptides assayed affected processes of egg development in 20-80% of ovarioles causing changes in the follicular epithelium, proliferation of its nuclei, and cell division toward the inner part of the egg chamber. This process leads to the occurrence of a multilayered follicular epithelium which later fills up almost the whole egg chamber and then degenerates. Such ovarioles are never able to produce eggs. The shortening of the peptide sequence accelerated the observed effects on egg development. The application of the (125)I-labeled peptides made possible to express quantitatively the time dependence of the radioactivity distribution in the insect body, including ovaries through which it is transferred to the next F1 generation. The radioactivity was measured in larvaes and, consequently, in newborn flies. For different peptide sequences applied, different radioactivity distributions in the insect body were found using the same radiolabeling. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1092

文献信息

• The C-Terminus Shortened Analogs of the Insect Peptide Oostatic Hormone with Accelerated Activity
  作者：Jan Hlaváček、Richard Tykva、Blanka Bennettová、Tomislav Barth

  DOI：10.1006/bioo.1998.1092

  日期：1998.10

  Shortened analogs 1a-1f of the oostatic hormone 1g with a decreased number or an omission of the C-terminal Pro residues were synthesized for investigation of their effect on oogenesis in the flesh fly Sarcophaga bullata Parker (Diptera). Peptides 1b-1g were prepared by solid-phase synthesis on polystyrene/divinylbenzene polymer with a 2-chlorotrityl linker using Fmoc/tBu strategy in dimethylformamide (DMF). Tetrapeptide Ia, devoid of all the carboxyterminal Pro residues, was prepared by stepwise procedure in DMF solution from HCl-H-Ala-OMe using Boc-Pro-OH, Z-Asp(OtBu)-OSu, and Boc-Tyr-OSu. In general, the peptides assayed affected processes of egg development in 20-80% of ovarioles causing changes in the follicular epithelium, proliferation of its nuclei, and cell division toward the inner part of the egg chamber. This process leads to the occurrence of a multilayered follicular epithelium which later fills up almost the whole egg chamber and then degenerates. Such ovarioles are never able to produce eggs. The shortening of the peptide sequence accelerated the observed effects on egg development. The application of the (125)I-labeled peptides made possible to express quantitatively the time dependence of the radioactivity distribution in the insect body, including ovaries through which it is transferred to the next F1 generation. The radioactivity was measured in larvaes and, consequently, in newborn flies. For different peptide sequences applied, different radioactivity distributions in the insect body were found using the same radiolabeling. (C) 1998 Academic Press.