N²-phenylacetyl-L-asparagine | 2752-49-0

• 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: N²-phenylacetyl-L-asparagine
• 英文别名: N²-Phenylacetyl-L-asparagin；Phenylacetylasparagine；(2S)-4-amino-4-oxo-2-[(2-phenylacetyl)amino]butanoic acid
• CAS: 2752-49-0
• 化学式: C₁₂H₁₄N₂O₄
• 分子量: 250.254
• InChiKey: OXZNUVREVMKPPC-VIFPVBQESA-N

物化性质

• 熔点：
  189-190 °C(Solv: water (7732-18-5))
• 沸点：
  634.8±55.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为产物：
  描述：

  L-天冬酰胺 、 苯乙酰氯 在 碳酸氢钠 作用下， 生成 N²-phenylacetyl-L-asparagine
  参考文献：
  名称：

  Kjaer, Acta Chemica Scandinavica (1947), 1952, vol. 6, p. 327,330

  摘要：

  DOI：

文献信息

• Verfahren zur Herstellung von Dipeptid-Additionsverbindungen und den daraus freigesetzten Dipeptiden
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0241864A2

  公开（公告）日：1987-10-21

  Bei der enzymatischen Verknüpfung von D-,L-Phenylalanin­alkylester oder L-Phenylalaninalkylester mit einer N-ge­schützten L-Asparaginsäure können eine Phenoxyacetyl-, Phenoxypropionyl- oder Phenylacetylgruppe als Aminoschutz­gruppe verwendet werden.

  在 D-、L-苯丙氨酸烷基酯或 L-苯丙氨酸烷基酯与 N-保护的 L-天冬氨酸的酶联过程中，可使用苯氧乙酰基、苯氧丙酰基或苯乙酰基作为氨基保护基团。
• 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.
• Method for purifying N-benzyloxycarbonyl aspartic acid
  申请人：PPG INDUSTRIES, INC.

  公开号：EP0072015B1

  公开（公告）日：1984-10-31
• EP1052968A4
  申请人：——

  公开号：EP1052968A4

  公开（公告）日：2004-09-15
• $g(a)-AMIDES OF $i(L)-AMINO ACIDS AS FRAGRANCE PRECURSORS
  申请人：THE GILLETTE COMPANY

  公开号：EP1052968A1

  公开（公告）日：2000-11-22