Z-Β-谷氨酸叔丁酯 | 118247-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: Z-Β-谷氨酸叔丁酯
• 英文名称: (3S)-3-(benzyloxycarbonylamino)-5-tert-butoxy-5-oxopentanoic acid
• 英文别名: (S)-3-(((Benzyloxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid；(3S)-5-[(2-methylpropan-2-yl)oxy]-5-oxo-3-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 118247-88-4
• 化学式: C₁₇H₂₃NO₆
• 分子量: 337.373
• InChiKey: ZWLHJIDBOFBLGR-ZDUSSCGKSA-N

物化性质

• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果按照规定使用和储存，则不会分解，没有已知的危险反应，请避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将贮藏器密封，并存放在阴凉、干燥处。确保工作环境有良好的通风或排气设施。

反应信息

• 作为反应物：
  描述：

  Z-Β-谷氨酸叔丁酯 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 生成 (S)-3-((R)-2-Amino-4-methyl-pentanoylamino)-4-phenethylcarbamoyl-butyric acid; compound with trifluoro-acetic acid
  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：

  1,3-丙酮二羧酸二甲酯 在 pig liver esterase 乙酸铵 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 phosphate buffer 、 3 A molecular sieve 、 sodium cyanoborohydride 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 16.58h， 生成 Z-Β-谷氨酸叔丁酯
  参考文献：
  名称：

  Crossley, Maxwell J.; Fisher, Megan L.; Potter, Jeffrey J., Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2363 - 2369

  摘要：

  DOI：

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.
• RODRIGUEZ, M.;FULCRAND, P.;LAUR, J.;AUMELAS, A.;BALI, J. P.;MARTINEZ, J., J. MED. CHEM., 32,(1989) N, C. 522-528
  作者：RODRIGUEZ, M.、FULCRAND, P.、LAUR, J.、AUMELAS, A.、BALI, J. P.、MARTINEZ, J.

  DOI：——

  日期：——
• WO2023/131690
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue
  作者：M. Rodriguez、P. Fulcrand、J. Laur、A. Aumelas、J. P. Bali、Jean Martinez

  DOI：10.1021/jm00123a003

  日期：1989.3

  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.
• Crossley, Maxwell J.; Fisher, Megan L.; Potter, Jeffrey J., Journal of the Chemical Society. Perkin transactions I, 1990, # 9, p. 2363 - 2369
  作者：Crossley, Maxwell J.、Fisher, Megan L.、Potter, Jeffrey J.、Kuchel, Philip W.、York, Michael J.

  DOI：——

  日期：——