N-(tert-butyloxycarbonyl)-L-tryptophanyl-5-bromo-DL-tryptophan | 129034-21-5

• 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: N-(tert-butyloxycarbonyl)-L-tryptophanyl-5-bromo-DL-tryptophan
• 英文别名: 3-(5-bromo-1H-indol-3-yl)-2-[[3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid
• CAS: 129034-21-5
• 化学式: C₂₇H₂₉BrN₄O₅
• 分子量: 569.455
• InChiKey: SWONJTNSPVNMOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  136.31
• 氢给体数：
  5.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(tert-butyloxycarbonyl)-L-tryptophanyl-5-bromo-DL-tryptophan 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以58%的产率得到L-tryptophanyl-5-bromo-DL-tryptophan
  参考文献：
  名称：

  Hemoglobin S antigelation agents based on 5-bromotryptophan with potential for sickle cell anemia

  摘要：

  5-Bromotryptophan (5-BrTrp) is the most potent amino acid derivative reported in the literature to inhibit the gelation of hemoglobin S (from sickle cell anemia patients). Trp-Trp is also more potent than Trp as an antigelation agent. Therefore, we have prepared a series of dipeptides containing 5-BrTrp and evaluated the antigelation activity. 5-BrTrp-5-BrTrp is the most potent, i.e., 5.9 times the activity of Trp, followed by 5-BrTrp-Trp and then Trp-5-BrTrp. This improved antigelation potency for 5-BrTrp-5-BrTrp and 5-BrTrp-Trp is very significant and will be pursued further as lead compounds with potential for sickle cell anemia.

  DOI：

  10.1021/jm00174a008
• 作为产物：
  描述：

  5-溴-DL-色氨酸 在 N-甲基哌啶 、 盐酸 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 0.61h， 生成 N-(tert-butyloxycarbonyl)-L-tryptophanyl-5-bromo-DL-tryptophan
  参考文献：
  名称：

  Hemoglobin S antigelation agents based on 5-bromotryptophan with potential for sickle cell anemia

  摘要：

  5-Bromotryptophan (5-BrTrp) is the most potent amino acid derivative reported in the literature to inhibit the gelation of hemoglobin S (from sickle cell anemia patients). Trp-Trp is also more potent than Trp as an antigelation agent. Therefore, we have prepared a series of dipeptides containing 5-BrTrp and evaluated the antigelation activity. 5-BrTrp-5-BrTrp is the most potent, i.e., 5.9 times the activity of Trp, followed by 5-BrTrp-Trp and then Trp-5-BrTrp. This improved antigelation potency for 5-BrTrp-5-BrTrp and 5-BrTrp-Trp is very significant and will be pursued further as lead compounds with potential for sickle cell anemia.

  DOI：

  10.1021/jm00174a008