N-phenylacetyl-L-glutamic acid | 2752-33-2

• 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: N-phenylacetyl-L-glutamic acid
• 英文别名: N-Phenylacetyl-L-glutaminsaeure；N-Phenylacetyl-L-glutaminsaeure；N-Phenylacetylglutamic acid；(2S)-2-[(2-phenylacetyl)amino]pentanedioic acid
• CAS: 2752-33-2
• 化学式: C₁₃H₁₅NO₅
• mdl: MFCD16378666
• 分子量: 265.266
• InChiKey: PTSRBZOZSRJCKX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-phenylacetyl-L-glutamic acid 在 乙酸酐 作用下， 生成 N-phenylacetyl-amino]-DL-glutamic acid-anhydride
  参考文献：
  名称：

  255. N-(N-phenylacetyl-α-DL-glutamyl)-D-penicillamine

  摘要：

  DOI：

  10.1039/jr9510001143
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 barium dihydroxide 作用下， 生成 N-phenylacetyl-L-glutamic acid
  参考文献：
  名称：

  Thierfelder; Sherwin, Chemische Berichte, 1914, vol. 47, p. 2632

  摘要：

  DOI：

文献信息

• Compositions for and uses thereof for treating viral disease with phenylacetate and derivatives thereof
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1108428A2

  公开（公告）日：2001-06-20

  A pharmaceutical composition for inhibiting viral replication and spread comprises a pharmaceutically effective amount of a compound of formula I:         R1R2CH-COOH wherein R1 is selected from H, CH3, CH3-O-, C2H5 or C3H7; R2 is selected from aryl X is wherein X is independently selected from halogen or hydroxy, and n is 0 to 4; a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and mixtures thereof together with a pharmaceutically acceptable carrier.

  一种用于抑制病毒复制和传播的药物组合物包含药用有效量的式 I 化合物： R1R2CH-COOH 其中 R1 选自 H、CH3、CH3-O-、C2H5 或 C3H7； R2 选自芳基 X 是 其中 X 独立选自卤素或羟基，且 n 为 0 至 4；其立体异构体或其药学上可接受的盐，以及其与药学上可接受的载体的混合物。
• Compositions for and uses thereof for altering gene expression with phenylacetate and derivatives thereof
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY OF THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1108427A2

  公开（公告）日：2001-06-20

  A pharmaceutical composition for inhibiting altering gene expression, inducing differentiation in nonmalignant mammalian cells, and for the treatment of β-chain hemoglobinopathies, comprises a pharmaceutically effective amount of a compound of formula I:         R1R2CH-COOH wherein R1 is selected from H, CH3, CH3-O-, C2H5 or C3H7; R2 is selected from X is wherein X is independently selected from halogen or hydroxy, and n is 0 to 4; a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and mixtures thereof together with a pharmaceutically acceptable carrier.

  一种用于抑制改变基因表达、诱导非恶性哺乳动物细胞分化和治疗 β 链血红蛋白病的药物组合物，包含药学有效量的式 I 化合物： R1R2CH-COOH 其中 R1 选自 H、CH3、CH3-O-、C2H5 或 C3H7； R2 选自 X 是 其中 X 独立选自卤素或羟基，且 n 为 0 至 4；其立体异构体或其药学上可接受的盐，以及其与药学上可接受的载体的混合物。
• Antiviral composition comprising phenylacetic acid derivatives
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1484059A2

  公开（公告）日：2004-12-08

  A pharmaceutical composition for inhibiting viral replication and spread comprises a pharmaceutically effective amount of a compound of formula I:         R1R2CH-COOH wherein    R1 is selected from H, CH3, CH3-O-, C2H5 or C3H7;    R2 is selected from aryl     (formulae of original claim 6) wherein X is independently selected from halogen or hydroxy, and n is 0 to 4; a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and mixtures thereof together with a pharmaceutically acceptable carrier.

  一种用于抑制病毒复制和传播的药物组合物包含药用有效量的式 I 化合物： R1R2CH-COOH 其中 R1 选自 H、CH3、CH3-O-、C2H5 或 C3H7； R2 选自芳基 (原权利要求 6 的式子) 其中 X 独立地选自卤素或羟基，且 n 为 0 至 4；其立体异构体或其药学上可接受的盐，以及其与药学上可接受的载体的混合物。
• Pharmaceutical composition for inhibiting altering gene expression and for inducing differentiation in non-malignant cells
  申请人：THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1484058A2

  公开（公告）日：2004-12-08

  A pharmaceutical composition for inhibiting altering gene expression, inducing differentiation in nonmalignant mammalian cells, and for the treatment of β-chain hemoglobinopathies, comprises a pharmaceutically effective amount of a compound of formula I:         R1R2CH-COOH wherein R1 is selected from H, CH3, CH3-O-, C2H5 or C3H7; R2 is selected from wherein X is independently selected from halogen or hydroxy, and n is 0 to 4; a stereoisomer thereof, or a pharmaceutically acceptable salt thereof, and mixtures thereof together with a pharmaceutically acceptable carrier.

  一种用于抑制改变基因表达、诱导非恶性哺乳动物细胞分化和治疗 β 链血红蛋白病的药物组合物，包含药学有效量的式 I 化合物： R1R2CH-COOH 其中 R1 选自 H、CH3、CH3-O-、C2H5 或 C3H7； R2 选自 其中 X 独立选自卤素或羟基，且 n 为 0 至 4；其立体异构体或其药学上可接受的盐，以及其与药学上可接受的载体的混合物。
• Preparation of d-amino acids by enzymatic kinetic resolution using a mutant of penicillin-G acylase from E. coli
  作者：Chiara Carboni、Hans G.T. Kierkels、Lucia Gardossi、Kamil Tamiola、Dick B. Janssen、Peter J.L.M. Quaedflieg

  DOI：10.1016/j.tetasy.2005.12.023

  日期：2006.1

  We have demonstrated for the first time that D-glutamine (D-Gln) and D-glutamic acid (D-Glu) can be efficiently obtained in high ee (97% and 90%, respectively) by enzymatic kinetic resolution of D,L-Gln and D,L-Glu. This was achieved by enantioselective conversion of the L-enantiomers to their N-phenylacetyl derivatives in aqueous solution, using a mutant of penicillin-G acylase (PGA) from E coli and phenylacetic acid methylester as the acyl donor. Kinetic modeling studies suggest that the high ee values obtained are both due to a strong enantiopreference for the L-amino acid in the deacylation step of the covalent enzyme intermediate, as well as to completeness of conversion that is transiently obtained as a result of the distinct preference of the mutant PGA for phenylacetic acid methylester over the N-phenylacetyl-L-amino acid product. For the other amino acids tested (Asn, Asp, and Ser), the highest ee values that were obtained for the remaining D-enantiomer are moderate (50-80%)because of lower enantioselectivity in the enzyme deacylation step and due to less complete conversion of the L-amino acid caused by competition for the active site between the acyl donor and the N-phenylacetyl-L-amino acid that is produced. The results demonstrate that the mutated PGA has great potential for the production of optically active D-amino acids by kinetic resolution. (c) 2006 Published by Elsevier Ltd.

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