(R,S)-N-benzyloxycarbonyl-2-aminopimelic acid diethyl ester | 256664-54-7

• 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: (R,S)-N-benzyloxycarbonyl-2-aminopimelic acid diethyl ester
• 英文别名: Diethyl 2-(phenylmethoxycarbonylamino)heptanedioate
• CAS: 256664-54-7
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: VELDTWPHEPIZSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R,S)-N-benzyloxycarbonyl-2-aminopimelic acid diethyl ester 在 Candida antarctica lipase B 、 三乙胺 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 反应 18.0h， 生成 2-Benzyloxycarbonylamino-6-[2-(4-benzyl-piperazin-1-yl)-ethylcarbamoyl]-hexanoic acid ethyl ester
  参考文献：
  名称：

  Lipase-catalysed synthesis of new acetylcholinesterase inhibitors: N-benzylpiperidine aminoacid derivatives

  摘要：

  New acetylcholinesterase inhibitors were synthetized via a lipase-mediated regioselective amidation using Candida antarctica lipase B as a biocatalyst in the key step. The new compounds have two different structural fragments: a N-benzylpiperidine moiety to anchor the enzyme active site and a dicarboxylic aminoacid to act as a biological carrier. Some analogues of N-benzylpiperazine were also synthesised and studied but they did not display AChE inhibitor activity. A preliminary structure-activity relationship study was performed employing some computational techniques as similarity indices and electrostatic potential maps. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00020-1
• 作为产物：
  描述：

  DL-2-氨基庚二酸 在 盐酸 作用下， 以 吡啶 、 水 为溶剂， 反应 64.0h， 生成 (R,S)-N-benzyloxycarbonyl-2-aminopimelic acid diethyl ester
  参考文献：
  名称：

  二羧基封闭氨基酸二酯的区域选择性脂肪酶催化酰胺化——侧链长度的影响

  摘要：

  当 (R)- 和 (S)-N- 封闭的 α-氨基己二酸和 α-氨基庚二酸的二乙酯在无水二异丙醚中受到南极念珠菌脂肪酶 B 催化的酰胺化时，它们仅产生 ω-单酰胺。这些结果与在相同实验条件下由等效的 L-谷氨酸衍生物产生的 α-单酰胺形成对比。这些结果表明侧链的长度在反应的区域选择性中起着至关重要的作用。

  DOI：

  10.1002/(sici)1099-0690(199911)1999:11<2835::aid-ejoc2835>3.0.co;2-t

文献信息

• Lipase-catalysed synthesis of new acetylcholinesterase inhibitors: N-benzylpiperidine aminoacid derivatives
  作者：Ana Martı́nez、Cristina Lanot、Concepción Perez、Ana Castro、Paloma López-Serrano、Santiago Conde

  DOI：10.1016/s0968-0896(00)00020-1

  日期：2000.4

  New acetylcholinesterase inhibitors were synthetized via a lipase-mediated regioselective amidation using Candida antarctica lipase B as a biocatalyst in the key step. The new compounds have two different structural fragments: a N-benzylpiperidine moiety to anchor the enzyme active site and a dicarboxylic aminoacid to act as a biological carrier. Some analogues of N-benzylpiperazine were also synthesised and studied but they did not display AChE inhibitor activity. A preliminary structure-activity relationship study was performed employing some computational techniques as similarity indices and electrostatic potential maps. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
• Regioselective Lipase-Catalysed Amidation of DicarboxylicN-Blocked Amino Acid Diesters – Effect of the Side-Chain Length
  作者：Santiago Conde、Paloma López-Serrano、Ana Castro、Ana Martínez

  DOI：10.1002/(sici)1099-0690(199911)1999:11<2835::aid-ejoc2835>3.0.co;2-t

  日期：1999.11

  α-aminopimelic acids yield exclusively the ω-monoamide when they are subjected to amidation catalysed by the lipase B of Candida antarctica in anhydrous diisopropyl ether. These results are in contrast to the α-monoamide yielded by the equivalent L-glutamic derivatives under the same experimental conditions. These results show that the length of the side chain plays a crucial role in the regioselectivity of the

  当 (R)- 和 (S)-N- 封闭的 α-氨基己二酸和 α-氨基庚二酸的二乙酯在无水二异丙醚中受到南极念珠菌脂肪酶 B 催化的酰胺化时，它们仅产生 ω-单酰胺。这些结果与在相同实验条件下由等效的 L-谷氨酸衍生物产生的 α-单酰胺形成对比。这些结果表明侧链的长度在反应的区域选择性中起着至关重要的作用。