methyl 2-methylene-1-(N-tert-butoxycarbonyl)aminocyclopropane-1-carboxylate | 426820-66-8

• 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: methyl 2-methylene-1-(N-tert-butoxycarbonyl)aminocyclopropane-1-carboxylate
• 英文别名: Methyl 2-methylidene-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 426820-66-8
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: YCVDENORSXDTLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-methylene-1-(N-tert-butoxycarbonyl)aminocyclopropane-1-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 45.0h， 以91%的产率得到1-amino-2-methylenecyclopropane-1-carboxylic acid hydrochloride
  参考文献：
  名称：

  Synthesis of Labeled 1-Amino-2-methylenecyclopropane- 1-carboxylic Acid, an Inactivator of 1-Aminocyclopropane-1-carboxylate Deaminase

  摘要：

  1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.

  DOI：

  10.1021/jo010994r
• 作为产物：
  描述：

  dimethyl 2-(tert-butyldimethylsilyloxy)methylcyclopropane-1,1-dicarboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 DOWEX-20W acidic resin 、 dicyclohexano-18-crown-6 、 potassium carbonate 、 氯乙酸乙酯 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 86.0h， 生成 methyl 2-methylene-1-(N-tert-butoxycarbonyl)aminocyclopropane-1-carboxylate
  参考文献：
  名称：

  Synthesis of Labeled 1-Amino-2-methylenecyclopropane- 1-carboxylic Acid, an Inactivator of 1-Aminocyclopropane-1-carboxylate Deaminase

  摘要：

  1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.

  DOI：

  10.1021/jo010994r

文献信息

• Synthesis of Labeled 1-Amino-2-methylenecyclopropane- 1-carboxylic Acid, an Inactivator of 1-Aminocyclopropane-1-carboxylate Deaminase
  作者：Zongbao Zhao、Hung-wen Liu

  DOI：10.1021/jo010994r

  日期：2002.4.1

  1-Amino-2-methylenecyclopropane-1-carboxylic acid (2-methylene-ACC) is an irreversible inhibitor for a bacterial enzyme, 1-aminocyclopropane-1-carboxylate (ACC) deaminase, which catalyzes the conversion of ACC to alpha-ketobutyrate and ammonia. The inactivation has been proposed to proceed with the ring scission induced by an addition of an enzyme nucleophile, resulting in the formation of a reactive turnover product that then traps an active-site residue. To gain further insight into this unique enzymatic reaction, the tritiated 2-methylene-ACC was prepared and incubated with ACC deaminase to locate and identify the entrapped amino acid residue. The synthesis of this radiolabeled compound and the results of its incubation with ACC deaminase are reported in this paper.