(3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid | 506444-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid
• 英文别名: (1S,2S)-2-[(4-methoxycarbonylphenyl)methoxycarbonylamino]cyclohex-3-ene-1-carboxylic acid
• CAS: 506444-80-0
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: QPIUQHAAXWTDKO-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid 在 lithium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 31.5h， 生成 (3S,4S)-3-(N'-p-hydroxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-N,N-dimethylcarboxamide
  参考文献：
  名称：

  Experimental Determination of the Absolute Enantioselectivity of an Antibody-Catalyzed Diels−Alder Reaction and Theoretical Explorations of the Origins of Stereoselectivity

  摘要：

  The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene- 1 carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition-state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.

  DOI：

  10.1021/ja020879d
• 作为产物：
  描述：

  4-(methoxycarbonyl)benzyl trans-1,3-butadiene-1-carbamate 在 lithium hydroxide 、 对叔丁基邻苯二酚 、 双氧水 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 74.0h， 生成 (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid
  参考文献：
  名称：

  Experimental Determination of the Absolute Enantioselectivity of an Antibody-Catalyzed Diels−Alder Reaction and Theoretical Explorations of the Origins of Stereoselectivity

  摘要：

  The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene- 1 carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition-state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.

  DOI：

  10.1021/ja020879d

文献信息

• Experimental Determination of the Absolute Enantioselectivity of an Antibody-Catalyzed Diels−Alder Reaction and Theoretical Explorations of the Origins of Stereoselectivity
  作者：Carina E. Cannizzaro、Jon A. Ashley、K. D. Janda、K. N. Houk

  DOI：10.1021/ja020879d

  日期：2003.3.1

  The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene- 1 carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition-state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.