乙基3-(2-萘基)丙氨酸酯 | 773841-83-1

• 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
• 中文名称: 乙基3-(2-萘基)丙氨酸酯
• 英文名称: (R)-2-naphthylalanine ethyl ester
• 英文别名: Ethyl 3-naphthalen-2-yl-D-alaninate；ethyl (2R)-2-amino-3-naphthalen-2-ylpropanoate
• CAS: 773841-83-1
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: WMWUVPBDJARXRB-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙基3-(2-萘基)丙氨酸酯 在 盐酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (R)-2-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-3-naphthalen-2-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Tripeptide growth hormone secretagogues

  摘要：

  A series of C-terminus capped dipeptides and tripeptides was synthesized as growth hormone (GH) secretagogues. Among them, tripeptide Aib-D-Trp-D-homoPhe-OEt showed low nanomolar activity in the rat pituitary assay. Thus, we have demonstrated that the GH secretagogue activity of the hexa- hepta-GH releasing peptides can be mimicked at the tripeptide level. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00103-6
• 作为产物：
  描述：

  (±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate 在 cobalt(II) chloride 作用下， 生成 L-3-(2-萘基)-丙氨酸 、 D-3-(2-萘基)-丙氨酸 、 乙基3-(2-萘基)丙氨酸酯
  参考文献：
  名称：

  Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine

  摘要：

  L-Aminoacylase from Aspergillus melleus was co-aggregated with polyethyleneimine and subsequently cross-linked with glutaraldehyde to obtain aminoacylase-polyethyleneimine cross-linked enzyme aggregates (termed as AP-CLEA). Under the optimum conditions, AP-CLEA expressed 74.9% activity recovery and 81.2% aggregation yield. The said method of co-aggregation and cross-linking significantly improved the catalytic stability of L-aminoacylase with respect to temperature and storage. AP-CLEA were employed for enantioselective synthesis of three unnatural amino acids (namely: phenylglycine, homophenylalanine and 2-naphthylalanine) via chiral resolution of their ester-. amide- and N-acetyl derivatives. The enantioselectivity of AP-CLEA was the highest for hydrolysis of amino acid amides; was moderate for hydrolysis of N-acetyl amino acids and was the least for hydrolysis of amino acid esters. Furthermore, AP-CLEA were found to retain more than 92% of the initial activity after five consecutive batches of (RS)-homophenylalanine hydrolysis suggesting an adequate operational stability of the biocatalyst. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.10.003

文献信息

• US8143052B2
  申请人：——

  公开号：US8143052B2

  公开（公告）日：2012-03-27
• Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine
  作者：Bhalchandra K. Vaidya、Suyog S. Kuwar、Sandeep B. Golegaonkar、Sanjay N. Nene

  DOI：10.1016/j.molcatb.2011.10.003

  日期：2012.2

  L-Aminoacylase from Aspergillus melleus was co-aggregated with polyethyleneimine and subsequently cross-linked with glutaraldehyde to obtain aminoacylase-polyethyleneimine cross-linked enzyme aggregates (termed as AP-CLEA). Under the optimum conditions, AP-CLEA expressed 74.9% activity recovery and 81.2% aggregation yield. The said method of co-aggregation and cross-linking significantly improved the catalytic stability of L-aminoacylase with respect to temperature and storage. AP-CLEA were employed for enantioselective synthesis of three unnatural amino acids (namely: phenylglycine, homophenylalanine and 2-naphthylalanine) via chiral resolution of their ester-. amide- and N-acetyl derivatives. The enantioselectivity of AP-CLEA was the highest for hydrolysis of amino acid amides; was moderate for hydrolysis of N-acetyl amino acids and was the least for hydrolysis of amino acid esters. Furthermore, AP-CLEA were found to retain more than 92% of the initial activity after five consecutive batches of (RS)-homophenylalanine hydrolysis suggesting an adequate operational stability of the biocatalyst. (C) 2011 Elsevier B.V. All rights reserved.
• Tripeptide growth hormone secretagogues
  作者：Lihu Yang、Greg Morriello、Yanping Pan、Ravi P. Nargund、Khaled Barakat、Kristine Prendergast、Kang Cheng、Wanda W.-S. Chan、Roy G. Smith、Arthur A. Patchett

  DOI：10.1016/s0960-894x(98)00103-6

  日期：1998.4

  A series of C-terminus capped dipeptides and tripeptides was synthesized as growth hormone (GH) secretagogues. Among them, tripeptide Aib-D-Trp-D-homoPhe-OEt showed low nanomolar activity in the rat pituitary assay. Thus, we have demonstrated that the GH secretagogue activity of the hexa- hepta-GH releasing peptides can be mimicked at the tripeptide level. (C) 1998 Elsevier Science Ltd. All rights reserved.