(tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-β-benzyl-L-aspartic acid amide | 92762-83-9

• 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: (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-β-benzyl-L-aspartic acid amide
• 英文别名: Boc-Gly-L-Trp-L-Met-L-Asp(Bzl)-NH2；benzyl (3S)-4-amino-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propanoyl]amino]-4-methylsulfanylbutanoyl]amino]-4-oxobutanoate
• CAS: 92762-83-9
• 化学式: C₃₄H₄₄N₆O₈S
• 分子量: 696.825
• InChiKey: YFKHEEJSIASQEC-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  236
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-β-benzyl-L-aspartic acid amide 在 Pd-BaSO₄ 氢气 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以65%的产率得到(tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide
  参考文献：
  名称：

  Synthesis and biological activity of new peptide segments of gastrin exhibiting gastrin antagonist property

  摘要：

  A series of C-terminal peptide segments of gastrin, i.e., (tert-butyloxycarbonyl)-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxy-carbonyl)-L-tyrosyl-glycyl-L-tryptophyl-L-methionyl-L-asp artic acid amide, and (benzyloxycarbonyl)-L-glutamyl-L-alanyl-L-tyrosyl-glycyl-L-tryptophyl-L -methionyl-L-aspartic acid amide were prepared and were shown to competitively inhibit the binding of labeled human gastrin to its receptors in an isolated gastric mucosal cell preparation and to antagonize the action of gastrin on gastric acid secretion (ED50 from 1.5 to 7 mg/kg) in vivo in the reperfused rat stomach, determined according to the method of Ghosh and Schild. From these studies, it could be concluded that the C-terminal phenylalanine residue, which is of primary importance for intrinsic biological gastrin-like activity, is not essential for binding to gastrin receptors.

  DOI：

  10.1021/jm00378a012
• 作为产物：
  描述：

  Boc-甘氨酸-4-硝基苯酯 、 (S)-3-{(S)-2-[(S)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-succinamic acid benzyl ester; compound with trifluoro-acetic acid 在 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-β-benzyl-L-aspartic acid amide
  参考文献：
  名称：

  Synthesis and biological activity of new peptide segments of gastrin exhibiting gastrin antagonist property

  摘要：

  A series of C-terminal peptide segments of gastrin, i.e., (tert-butyloxycarbonyl)-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxy-carbonyl)-L-tyrosyl-glycyl-L-tryptophyl-L-methionyl-L-asp artic acid amide, and (benzyloxycarbonyl)-L-glutamyl-L-alanyl-L-tyrosyl-glycyl-L-tryptophyl-L -methionyl-L-aspartic acid amide were prepared and were shown to competitively inhibit the binding of labeled human gastrin to its receptors in an isolated gastric mucosal cell preparation and to antagonize the action of gastrin on gastric acid secretion (ED50 from 1.5 to 7 mg/kg) in vivo in the reperfused rat stomach, determined according to the method of Ghosh and Schild. From these studies, it could be concluded that the C-terminal phenylalanine residue, which is of primary importance for intrinsic biological gastrin-like activity, is not essential for binding to gastrin receptors.

  DOI：

  10.1021/jm00378a012

文献信息

• Structure-activity relationships of C-terminal tri- and tetrapeptide fragments that inhibit gastrin activity
  作者：Jean Martinez、Jean Pierre Bali、Richard Magous、Janine Laur、Marie Francoise Lignon、Christian Briet、Dino Nisato、Bertrand Castro

  DOI：10.1021/jm00381a002

  日期：1985.3

  A series of tri- and tetrapeptide derivatives, analogues of the gastrin C-terminal region with no phenylalanine residue, were synthesized. These peptides were tested for their ability to inhibit gastrin-stimulated acid secretion in vivo as well as binding of [125I]-(Nle11)-HG-13 to gastric mucosal cell receptors in vitro. Most of the peptides tested exhibited gastrin antagonist activity in vivo and in vitro. Most active derivatives were 20-30 times more potent than the well-known gastrin antagonist derivatives proglumide and benzotript and had 20-200 times more binding affinity. The smallest fragment exhibiting antagonist activity was the tripeptide Boc-L-tryptophyl-L-methionyl-L-aspartic acid amide.