(2S,1'S,2'S)-2-(2'-carboxycyclobutyl)glycine

• 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: (2S,1'S,2'S)-2-(2'-carboxycyclobutyl)glycine
• 英文别名: (1S,2S)-2-[(S)-amino(carboxy)methyl]cyclobutane-1-carboxylic acid
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: SRAFHGOPGVYULO-YUPRTTJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  cis-1,2-cyclobutane dicarboxylic anhydride 在 4-二甲氨基吡啶 、 lithium hydroxide 、 L-谷氨酸 、 E_. coli branched chain aminotransferase 、 臭氧 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 70.0h， 生成 (2S,1'S,2'S)-2-(2'-carboxycyclobutyl)glycine
  参考文献：
  名称：

  Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

  摘要：

  Optically pure trans-cyclobutane analogues of glutamic acid are prepared by highly selective enzymatic transamination of a single racemic trans-cyclobutane alpha-ketoglutaric acid derivative 5, which is synthesized in five steps from maleic anhydride. (2S,1'R,2'R)- and (2S,I'S,2'S)-2-(2'-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I are obtained using aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT), respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.156

文献信息

• Stereoselective Chemoenzymatic Synthesis of the Four Stereoisomers of <scp>l</scp>-2-(2-Carboxycyclobutyl)glycine and Pharmacological Characterization at Human Excitatory Amino Acid Transporter Subtypes 1, 2, and 3
  作者：Sophie Faure、Anders A. Jensen、Vincent Maurat、Xin Gu、Emmanuelle Sagot、David J. Aitken、Jean Bolte、Thierry Gefflaut、Lennart Bunch

  DOI：10.1021/jm060822s

  日期：2006.11.1

  the corresponding cis and trans-2-oxalylcyclobutanecarboxylic acids 5 and 6 using the enzymes aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT) from Escherichia coli. The four stereoisomeric compounds were evaluated as potential ligands for the human excitatory amino acid transporters, subtypes 1, 2, and 3 (EAAT1, EAAT2, and EAAT3) in the FLIPR membrane potential assay. While

  以高收率和高对映体过量合成了l-2-（2-羧基环丁基）甘氨酸，l-CBG-I，l-CBG-II，l-CBG-III和l-CBG-IV的四种立体异构体，使用大肠杆菌的天冬氨酸氨基转移酶（AAT）和支链氨基转移酶（BCAT）从相应的顺式和反式-2-草酰环丁烷羧酸5和6中提取。在FLIPR膜电位测定法中，将四种立体异构体化合物评估为人类兴奋性氨基酸转运蛋白亚型1、2和3（EAAT1，EAAT2和EAAT3）的潜在配体。虽然一个反式立体异构体1-CBG-I在所有三个转运蛋白EAAT1-3上均显示较弱的底物活性，但我们发现另一种反式立体异构体1-CBG-II具有特定的药理学特征，其显示了EAAT1底物活性。以及对EAAT2和EAAT3的抑制活性。
• Photocycloaddition of α,β-unsaturated-γ-lactam with ethylene. Synthesis of conformationally restricted glutamate analogs, l-2-(2-carboxycyclobutyl)glycines
  作者：Hidekazu Tsujishima、Kuniko Nakatani、Keiko Shimamoto、Yasushi Shigeri、Noboru Yumoto、Yasufumi Ohfune

  DOI：10.1016/s0040-4039(97)10807-3

  日期：1998.3

  Both (2S,1′S,2′S)- and (2S,1′S,2′R)-isomers of 2-(2-carboxycyclobutyl)glycine (CBG-I, 1b) and (CBG-III, 2b) are synthesized in a stereoselective manner via a [2+2] photocycloaddition of α,β-unsaturated-γ-lactam 3 with ethylene in acetone. The extended type of isomer 1b showed a weak activity on group II metabotropic glutamate receptors (mGluR2) of rat brain.

  两（2小号，1'小号，2'小号） -和（2小号，1'小号，2' - [R 2-（2- carboxycyclobutyl）甘氨酸（CBG-1，） -异构体1B）和（CBG-III ，2b）通过α，β-不饱和-γ-内酰胺3与乙烯在丙酮中的[2 + 2]光环加成以立体选择的方式合成。异构体1b的扩展类型对大鼠脑的II型代谢型谷氨酸受体（mGluR2）具有弱活性。
• NON-AQUEOUS ELECTROLYTE FOR LITHIUM-ION BATTERY
  申请人：UCHICAGO ARGONNE, LLC

  公开号：US20140186721A1

  公开（公告）日：2014-07-03

  An electrolyte including an alkali metal salt; a polar aprotic solvent; and a triazinane trione; wherein the electrolyte is substantially non-aqueous.
• US9218915B2
  申请人：——

  公开号：US9218915B2

  公开（公告）日：2015-12-22
• Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination
  作者：Xin Gu、Mo Xian、Sophie Roy-Faure、Jean Bolte、David J. Aitken、Thierry Gefflaut

  DOI：10.1016/j.tetlet.2005.10.156

  日期：2006.1

  Optically pure trans-cyclobutane analogues of glutamic acid are prepared by highly selective enzymatic transamination of a single racemic trans-cyclobutane alpha-ketoglutaric acid derivative 5, which is synthesized in five steps from maleic anhydride. (2S,1'R,2'R)- and (2S,I'S,2'S)-2-(2'-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I are obtained using aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT), respectively. (c) 2005 Elsevier Ltd. All rights reserved.