(S)-N-(phenylacetyl)-α-phenylglycinonitrile | 345643-03-0

• 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: (S)-N-(phenylacetyl)-α-phenylglycinonitrile
• 英文别名: N-[(S)-cyano(phenyl)methyl]-2-phenylacetamide
• CAS: 345643-03-0
• 化学式: C₁₆H₁₄N₂O
• 分子量: 250.3
• InChiKey: GGJZXZFZJDWHBC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(phenylacetyl)-α-phenylglycinonitrile 在 盐酸 、 sodium hydroxide 、 E_. coli penicillin acylase 作用下， 以 水 为溶剂， 生成 苯乙酸 、 (S)-氨基(苯基)乙腈
  参考文献：
  名称：

  Resolution of (RS)-phenylglycinonitrile by penicillin acylase-catalyzed acylation in aqueous medium

  摘要：

  A new strategy for the biocatalytic resolution of (R,S)-phenylglycinonitrile, a crucial intermediate in the antibiotic industry, has been developed. While former techniques exploit nitrilases or combinations of nitrile hydratases and amidases, manipulating with nitrile functionality, the Current approach is based on a highly efficient and enantioselective acylation of the alpha-amino group with phenylacetic acid catalyzed by a well known enzyme, penicillin acylase from E. coli, in slightly acidic aqueous medium. It is shown that since the condensation product is poorly soluble, removal of (S)-phenylglycinonitrile from the reaction sphere is almost complete and irreversible, favoring kinetics of the process and making high conversion possible. The proposed approach is characterized by high space-time yield and extends the scope of enzymatic synthesis in aqueous medium. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00523-8
• 作为产物：
  描述：

  苯乙酸乙酯 、 2-amino-2-phenylacetonitrile 在 Novozym 435 、 Zeolite NaA 作用下， 以 异丙醚 为溶剂， 反应 24.0h， 以47%的产率得到(S)-N-(phenylacetyl)-α-phenylglycinonitrile
  参考文献：
  名称：

  Enantioselective acylation of α-aminonitriles catalysed by Candida antarctica lipase. An unexpected turnover-related racemisation

  摘要：

  Candida antarctica lipase B (Novozyme 435) catalysed the enantioselective acylation of 2-amino-2-phenylacetonitrile 1 with ethyl phenylacetate affording a near enantiopure product in 47% yield. Acylation of 1 and 2-amino-4-phenylbutyronitrile with ethyl acetate yielded an unexpected partially racemised final product. The racemisation was shown to be turnover related and is ascribed to the increased acidity of the alpha -proton in the formation of the tetrahedral intermediate in the active site of the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00011-8

文献信息

• Enantioselective acylation of α-aminonitriles catalysed by Candida antarctica lipase. An unexpected turnover-related racemisation
  作者：P. López-Serrano、J.A. Jongejan、F. van Rantwijk、R.A. Sheldon

  DOI：10.1016/s0957-4166(01)00011-8

  日期：2001.2

  Candida antarctica lipase B (Novozyme 435) catalysed the enantioselective acylation of 2-amino-2-phenylacetonitrile 1 with ethyl phenylacetate affording a near enantiopure product in 47% yield. Acylation of 1 and 2-amino-4-phenylbutyronitrile with ethyl acetate yielded an unexpected partially racemised final product. The racemisation was shown to be turnover related and is ascribed to the increased acidity of the alpha -proton in the formation of the tetrahedral intermediate in the active site of the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Resolution of (RS)-phenylglycinonitrile by penicillin acylase-catalyzed acylation in aqueous medium
  作者：Ghermes G. Chilov、Harold M. Moody、Wilhelmus H.J. Boesten、Vytas K. Švedas

  DOI：10.1016/s0957-4166(03)00523-8

  日期：2003.9

  A new strategy for the biocatalytic resolution of (R,S)-phenylglycinonitrile, a crucial intermediate in the antibiotic industry, has been developed. While former techniques exploit nitrilases or combinations of nitrile hydratases and amidases, manipulating with nitrile functionality, the Current approach is based on a highly efficient and enantioselective acylation of the alpha-amino group with phenylacetic acid catalyzed by a well known enzyme, penicillin acylase from E. coli, in slightly acidic aqueous medium. It is shown that since the condensation product is poorly soluble, removal of (S)-phenylglycinonitrile from the reaction sphere is almost complete and irreversible, favoring kinetics of the process and making high conversion possible. The proposed approach is characterized by high space-time yield and extends the scope of enzymatic synthesis in aqueous medium. (C) 2003 Elsevier Ltd. All rights reserved.