(S)-N-benzyloxycarbonyl-2-aminoadipic acid diethyl ester | 256664-48-9

• 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: (S)-N-benzyloxycarbonyl-2-aminoadipic acid diethyl ester
• 英文别名: diethyl (S)-2-(((benzyloxy)carbonyl)amino)hexanedioate；diethyl (2S)-2-(phenylmethoxycarbonylamino)hexanedioate
• CAS: 256664-48-9
• 化学式: C₁₈H₂₅NO₆
• 分子量: 351.4
• InChiKey: OIJNKEMDKLMRPJ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-N-benzyloxycarbonyl-2-aminoadipic 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 17.0h， 生成 6-(N-benzylpiperazinyl-2-ethylamido)-N-benzyloxycarbonyl-S-α-amino-adipic acid 1-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：

  L-2-氨基己二酸 在 盐酸 作用下， 以 吡啶 、 水 为溶剂， 反应 64.0h， 生成 (S)-N-benzyloxycarbonyl-2-aminoadipic 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

• Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling
  作者：Ze-Peng Yang、Dylan J. Freas、Gregory C. Fu

  DOI：10.1021/jacs.1c03903

  日期：2021.6.16

  enantioconvergent coupling of readily available racemic alkyl electrophiles with a wide variety of alkylzinc reagents (1:1.1 ratio) to afford protected unnatural α-amino acids in good yield and ee. This cross-coupling, which proceeds under mild conditions and is tolerant of air, moisture, and a broad array of functional groups, complements earlier approaches to the catalytic asymmetric synthesis of this valuable family

  近年来，从蛋白质设计到药物化学再到材料科学等领域，人们对非天然 α-氨基酸的兴趣迅速增加。因此，开发高效、通用和直接的对映选择性合成方法是反应开发的重要目标。在本报告中，我们确定了一种基于镍（一种地球丰富的金属）的手性催化剂，可以实现容易获得的外消旋烷基亲电子试剂与多种烷基锌试剂（1:1.1 的比例）的对映收敛偶联，以提供受保护的非天然 α-氨基酸产量和ee值都很好。这种交叉偶联在温和的条件下进行，耐受空气、水分和广泛的官能团，补充了这一有价值的分子家族的催化不对称合成的早期方法。我们已将我们的新方法应用于生成几种对映体富集的非天然 α-氨基酸，这些氨基酸先前已被证明可作为生物活性化合物合成中的有用中间体。
• 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。