Gly-CAM trifluoroacetate | 95496-21-2

• 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: Gly-CAM trifluoroacetate
• CAS: 95496-21-2
• 化学式: C₂HF₃O₂*C₄H₈N₂O₃
• 分子量: 246.143
• InChiKey: FJLTXSZKHDRURT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.39
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132.71
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-硝基苯基N-{[(2-甲基-2-丙基)氧基]羰基}-L-酪氨酸酯 、 Gly-CAM trifluoroacetate 在 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)-L-tyrosyl-glycine carbamoylmethyl ester
  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：

  (tert-butyloxycarbonyl)glycine carbamoylmethyl ester 在 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 Gly-CAM trifluoroacetate
  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

• On the use of carboxamidomethyl esters (cam esters) in the synthesis of model peptides. scope and limitations
  作者：Jean Martinez、Janine Laur、Bertrand Castro

  DOI：10.1016/s0040-4020(01)96451-8

  日期：1985.1

  protecting group for peptide synthesis was demonstrated. The synthesis of the chemotactic peptide For-Met-Leu-Phe-OH as well as the synthesis of Met-enkephalin using CAM ester as carboxyl terminal protection were performed. These esters showed good stability during acidolytic removal of BOC N-protecting group, during hydrogenolysis of Z N-protecting group and during removal of FMOC N-protecting group. CAM

  证明了羧酰胺基甲基酯（CAM酯）作为用于肽合成的羧基保护基的用途。进行了趋化肽For-Met-Leu-Phe-OH的合成以及使用CAM酯作为羧基末端保护的Met-脑啡肽的合成。这些酯在酸解去除BOC N-保护基期间，Z N-保护基的氢解期间和FMOC N-保护基的去除期间显示出良好的稳定性。CAM酯可被NaOH 0.5 N或Na 2 CO 3迅速裂解。但是，当序列中存在天冬氨酸的β-苄基酯时，我们未能成功地选择性除去CAM酯。