Z-D-Asp(OBut)-CHN2 | 118248-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z-D-Asp(OBut)-CHN2
• CAS: 118248-05-8
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: FPGXCBCOUDLSSD-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118.1
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-D-Asp(OBut)-CHN2 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 silver benzoate 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 40.5h， 生成
  参考文献：
  名称：

  Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue

  摘要：

  A series of analogues of Boc-Trp-Leu-Asp-Phe-NH2, a potent gastrin agonist, were synthesized by introducing a beta-homo residue in the sequence. These compounds were tested in vivo on acid secretion, in the anesthetized rat, and for their ability to inhibit binding of labeled gastrin to its receptors on gastric mucosal cells. These analogues behaved as gastrin antagonists. The most potent compounds in this series were Boc-Trp-Leu-beta-homo-Asp-NHCH2C6H5 (10) (IC50 = 1 microM, ED50 = 0.2 mg/kg), Boc-Trp-Leu-beta-homo-Asp-NHCH2CH2C6H5 (11) (IC50 = 0.75 microM, ED50 = 0.5 mg/kg), Boc-Trp-Leu-beta-homo-Asp-Phe-NH2 (12) (IC50 = 1.5 microM, ED50 = 0.1 mg/kg), and Boc-Trp-Leu-beta-homo-Asp-D-Phe-NH2 (13) (IC50 = 2 microM, ED50 = 0.1 mg/kg). We could demonstrate the importance of the region of the peptide bond between leucine and aspartic acid and of the structure of the C-terminal dipeptide Asp-Phe-NH2, for exhibiting biological activity on acid secretion.

  DOI：

  10.1021/jm00123a003
• 作为产物：
  描述：

  Cbz-D-天冬氨酸 4-叔丁酯一水物 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Z-D-Asp(OBut)-CHN2
  参考文献：
  名称：

  嘧啶酮抗生素-具有改善的抗菌谱的杂环类似物。

  摘要：

  我们报告了天然二肽抗生素TAN 1057 A，B的新衍生物的合成和药理学评估，该衍生物在β-氨基酸侧链中或作为尿素功能的模拟物含有杂环。在该程序的过程中，我们确定了显示对更广泛的革兰氏阳性细菌具有活性的新型类似物。

  DOI：

  10.1016/s0960-894x(03)00578-x

文献信息

• Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)
  作者：Sándor Bajusz、Irén Fauszt、Klára Németh、Éva Barabás、Attila Juhász、Miklós Patthy

  DOI：10.1016/s0960-894x(98)00244-3

  日期：1998.6

  Inhibition of interleukin-1 beta converting enzyme (ICE), apopain, papain, thrombin and trypsin with substrate like peptidyl L- and D-alpha-aldehydes and their L-beta-homo-aldehyde analogues was investigated. The L-beta-homo-aspartals appear to be specific inhibitors for ICE and its homologues; the other enzymes were not inhibited with such L-beta-homo aldehydes. Papain shows tolerance for D-residues at P-1 depending on their chiral stability. (C) 1998 Elsevier Science Ltd. All rights reserved.