D-CCG-IV | 125412-13-7

• 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: D-CCG-IV
• 英文别名: (2R,3S,4R) α-(Carboxycyclopropyl)glycine；(1R,2S)-2-[(R)-amino(carboxy)methyl]cyclopropane-1-carboxylic acid
• CAS: 125412-13-7
• 化学式: C₆H₉NO₄
• 分子量: 159.142
• InChiKey: GZOVEPYOCJWRFC-PZGQECOJSA-N

物化性质

• 沸点：
  414.1±20.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-[(R)-1-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-cyclopropanecarboxylic acid ethyl ester 在 sodium hydroxide 、 jones reagent 、 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 16.0h， 生成 D-CCG-IV
  参考文献：
  名称：

  Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs

  摘要：

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.

  DOI：

  10.1021/jo00013a018

文献信息

• D-3,4-‘cyclopropylglutamate’ isomers as nmda receptor ligands: Synthesis and enantioselective activity.
  作者：Roberto Pellicciari、Benedetto Natalini、Maura Marinozzi、Joseph B Monahan、James P Snyder

  DOI：10.1016/s0040-4039(00)94355-7

  日期：1990.1

  D-Cbz-vinylglycine methyl ester (11) afforded a mixture of the cyclopropyl esters D-CGA A-D (13) from which the corresponding 2R-acids 7-10 were obtained and their absolute configurations assigned. The (2R,3S,4R) α-(carboxycyclopropyl)glycine (D-CGA C, 9 resulted to be the most potent and selective among the NMDA receptor ligands yet reported.

  二铑（II）四乙酸催化在d-CBZ-乙烯基甘氨酸甲基酯的存在重氮乙酸乙酯的分解（11） ，得到环丙基酯d-CGA AD的混合物（13），从该相应2R酸7-10得到及其绝对配置。结果表明，（2R，3S，4R）α-（羧基环丙基）甘氨酸（D-CGA C，9）在迄今为止报道的NMDA受体配体中是最有效和最具选择性的。
• PELLICCIARI, ROBERTO;NATALINI, BENEDETTO;MARINOZZI, MAURA;MONAHAN, JOSEPH+, TETRAHEDRON LETT., 31,(1990) N, C. 139-142
  作者：PELLICCIARI, ROBERTO、NATALINI, BENEDETTO、MARINOZZI, MAURA、MONAHAN, JOSEPH+

  DOI：——

  日期：——
• Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogs
  作者：Keiko Shimamoto、Michiko Ishida、Haruhikio Shinozaki、Yasufumi Ohfune

  DOI：10.1021/jo00013a018

  日期：1991.6

  To determine what conformations of L-glutamate (L-Glu) activate that compound's different receptors in the mammalian central nervous system, four diastereomeric L-2-(carboxycyclopropyl)glycines, 1-4, which are conformationally constrained analogues of the extended and folded conformers of L-Glu, were synthesized and subjected to neutrophysiological assay. Compounds 1-4 were efficiently synthesized from chiral amino acids. Cyclopropanation of the (2S)-2-amino-3-butenol derivative 5b gave intermediates for the synthesis of all four diastereomers. Stereoselective cyclopropanation of both the alpha,beta-unsaturated gamma-lactam 16 and the delta-lactone 19 gave precursors of (2S,1'S,2'R)-3 and (2S,1'R,2'S)-4, respectively. Neurophysiological assays of 1-4 performed with the newborn rat spinal cord demonstrated that the compounds induced a variety of depolarizing effects. The results of the assays strongly suggested that the N-methyl-D-aspartic acid (NMDA) receptor is activated by the folded conformer of L-Glu and that the extended conformer of L-Glu activates the metabotropic L-Glu receptor. The four analogous D-2-(carboxycyclopropyl)glycines (D-1-D-4), which were synthesized from (2R)-5b, proved to be NMDA agonists.