dimethyl (S)-2-[2-(benzyloxycarbonylamino)acetylamino]pentanedioate | 4817-87-2

• 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: dimethyl (S)-2-[2-(benzyloxycarbonylamino)acetylamino]pentanedioate
• 英文别名: Cbz-Gly-L-Glu(OMe)-OMe；dimethyl (2S)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]pentanedioate
• CAS: 4817-87-2
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: UKEIAGSMBRYYDC-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl (S)-2-[2-(benzyloxycarbonylamino)acetylamino]pentanedioate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.3 kPa 条件下， 反应 16.0h， 以85%的产率得到dimethyl (S)-3-(3,6-dioxopiperazin-2-yl)propionate
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1
• 作为产物：
  描述：

  L-谷氨酸 在 N-乙基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 dimethyl (S)-2-[2-(benzyloxycarbonylamino)acetylamino]pentanedioate
  参考文献：
  名称：

  Synthesis of chiral non-racemic 3-(dioxopiperazin-2-yl)propionic acid derivatives

  摘要：

  Starting with the proteinogenic amino acid (S)-glutamate (3) a facile, high yielding synthesis of the chiral non-racemic 3-(dioxo-piperazin-2-yl)propionates 6, 11, and 14 is presented. Key intermediates in the synthesis of Ne-benzyl substituted (dioxopiperazin-2-yl)propionates 11 and 14 are the N-monobenzylglutamate 8 and the chloroacetamide 12, which allow introduction of various substituents in position 4 of the piperazine ring. In receptor binding studies with radioligands the 3-(piperazin-2-yl)propanol 15 was found to have promising affinity for sigma(1)-receptors (K-i=66.1 nM). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01212-1

文献信息

• Bromelain Catalyzed Synthesis of Peptides in Organic Solvent
  作者：Dar-Fu Tai、Shu-Lin Fu

  DOI：10.1002/jccs.200300025

  日期：2003.2

  exported by Taiwan. There is no deficiency for thesource of this enzyme. Therefore, the application of bro-melain to catalyze the synthesis of peptides has great poten-tial and economic value.No research effort has ever been made in peptide syn-thesis using bromelain except for catalyzing polymerizationin aqueous solution.

  是一种来自菠萝茎提取物的硫醇蛋白酶。菠萝是台湾丰富的资源。菠萝蛋白酶（EC.3,4,4,24）是台湾出口的两种主要酶之一。这种酶的来源没有缺陷。因此，将菠萝蛋白酶应用于催化多肽合成具有巨大的潜力和经济价值。除在水溶液中催化聚合外，目前还没有利用菠萝蛋白酶合成多肽的研究成果。