tert-butoxycarbonyl-α-L-glutamyl-p-cyanoanilide γ-benzyl ester | 927191-10-4

• 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-butoxycarbonyl-α-L-glutamyl-p-cyanoanilide γ-benzyl ester
• 英文别名: O⁵-benzyl-N^α-tert-butyloxycarbonyl-N'-(4-cyanophenyl)-L-glutamic amide；benzyl (4S)-5-(4-cyanoanilino)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 927191-10-4
• 化学式: C₂₄H₂₇N₃O₅
• 分子量: 437.495
• InChiKey: LSQMYHMBMNULCQ-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyl-α-L-glutamyl-p-cyanoanilide γ-benzyl ester 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 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
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 tert-butoxycarbonyl-α-L-glutamyl-p-cyanoanilide γ-benzyl ester
  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

• Efficient Amidation from Carboxylic Acids and Azides via Selenocarboxylates:  Application to the Coupling of Amino Acids and Peptides with Azides
  作者：Xinghua Wu、Longqin Hu

  DOI：10.1021/jo061703n

  日期：2007.2.1

  A facile one-pot procedure for the coupling of carboxylic acid and azide via selenocarboxylate and selenatriazoline has been developed and successfully applied to the coupling of amino acids and peptides with azides. Selenocarboxylates are readily prepared by the reaction of the activated carboxylic acids with LiAlHSeH under mild conditions. The selenocarboxylates formed in situ are used to react directly

  已经开发了一种简单的一锅法，用于通过硒代羧酸盐和硒代三唑啉偶联羧酸和叠氮化物，并将其成功地用于氨基酸和肽与叠氮化物的偶联。通过在温和条件下使活化的羧酸与LiAlHSeH反应，可以轻松制备硒代羧酸盐。原位形成的硒羧酸盐用于通过硒代三唑啉中间体与叠氮化物直接反应形成相应的酰胺。对于缺乏电子的叠氮化物，获得了优异的产率，对于富含电子的叠氮化物，获得了中等至良好的产率。硒代羧酸酯/叠氮化物酰胺化反应是清洁的和化学选择性的。