trifluoroacetyl-α-L-glutamyl-p-cyanoanilide | 77314-15-9

• 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: trifluoroacetyl-α-L-glutamyl-p-cyanoanilide
• 英文别名: (4S)-5-(4-cyanoanilino)-5-oxo-4-[(2,2,2-trifluoroacetyl)amino]pentanoic acid
• CAS: 77314-15-9
• 化学式: C₁₄H₁₂F₃N₃O₄
• 分子量: 343.262
• InChiKey: BVKPTAWUJKLCEO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 sodium hydroxide 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.25h， 生成 trifluoroacetyl-α-L-glutamyl-p-cyanoanilide
  参考文献：
  名称：

  Peptide sweeteners. 5. Side chain homologs relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners

  摘要：

  Side-chain homologues of sweet trifluoroacetyl-alpha-L-aspartyl-p-cyanoanilide have been synthesized and tasted. Removal of the trifluoroacetyl group only changes the potency of sweet taste, not the taste property. These results have been compared with the structure-taste relationships of dipeptide sweeteners. An informative discontinuity of taste effects was found to exist with novel aminomalonyl dipeptide derivatives. The results are explained on topochemical grounds.

  DOI：

  10.1021/jm00346a013

文献信息

• Peptide sweeteners. 5. Side chain homologs relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners
  作者：Masao Kawai、Rolf Nyfeler、Judd M. Berman、Murray Goodman

  DOI：10.1021/jm00346a013

  日期：1982.4

  Side-chain homologues of sweet trifluoroacetyl-alpha-L-aspartyl-p-cyanoanilide have been synthesized and tasted. Removal of the trifluoroacetyl group only changes the potency of sweet taste, not the taste property. These results have been compared with the structure-taste relationships of dipeptide sweeteners. An informative discontinuity of taste effects was found to exist with novel aminomalonyl dipeptide derivatives. The results are explained on topochemical grounds.