(R)-homophenylalanine amide | 85808-34-0

• 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: (R)-homophenylalanine amide
• 英文别名: (R)-2-amino-4-phenyl-butyric acid amide；(R)-2-Amino-4-phenyl-buttersaeure-amid；(R,S)-2-Amino-4-phenyl-butyramide；(2R)-2-amino-4-phenylbutanamide
• CAS: 85808-34-0；99169-43-4；124019-00-7
• 化学式: C₁₀H₁₄N₂O
• 分子量: 178.234
• InChiKey: XSJXYGRSPMLWNS-SECBINFHSA-N

物化性质

• 熔点：
  89-90 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  368.7±42.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-homophenylalanine amide 在 盐酸 作用下， 生成 D-苯基丁氨酸
  参考文献：
  名称：

  氨基酸的分辨率。I. 亮氨酸氨肽酶拆分外消旋苯丙氨酸和γ-苯基-α-氨基丁酸

  摘要：

  DL-苯丙酰胺和DL-苯基-氨基丁酸酰胺通过部分纯化的亮氨酸氨肽酶制剂拆分为L-氨基酸和D-氨基酸酰胺。对于 DL-苯丙酰胺，使用离子交换树脂 Amberlite IRA-400 可以方便地分离消化物中的产物，而对于 DL-苯氨基丁酰胺，则使用不同的溶解度。得到的D-氨基酸酰胺盐酸盐部分经酸水解转化为D-氨基酸。

  DOI：

  10.1246/bcsj.31.529
• 作为产物：
  描述：

  DL-高苯丙氨酸 在 盐酸 、 Candida antarctica lipase B 、 Novo SP₆₁₁ 、 Zeolite NaA 、 氨 作用下， 以 叔丁醇 为溶剂， 反应 40.0h， 生成 (R)-homophenylalanine amide
  参考文献：
  名称：

  Enantioselective enzyme catalysed ammoniolysis of amino acid derivatives. Effect of temperature

  摘要：

  The lipases from Candida antarctica (B type), Thermomyces lanuginosus and Pseudomonas alcaligenes catalysed the enantioselective ammoniolysis of free amino acid esters. In the ammoniolysis of phenylalanine methyl ester catalysed by T. lanuginosus lipase a decrease in temperature to -20 degreesC significantly enhanced the enantioselectivity up to an enantiomeric ratio (E) of 84. Several proteases efficiently catalysed the ammoniolysis of N-BOC protected amino acid esters with nearly absolute enantioselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00023-4

文献信息

• Process for preparation of organic chemicals
  申请人：NOVO NORDISK A/S

  公开号：EP0307023A1

  公开（公告）日：1989-03-15

  Process for the racemization of an amino acid amide with the general Formula I the amino acid amide being brought into contact with an en­zyme with amino acid amide racemase activity. In particular the invention relates to a process for enzymatic preparation of optically active amino acids from amino acid amides by bringing the amino acid amide into contact with a biocatalyst which in addition possesses L- or D-amidase activity.

  通式 I 氨基酸酰胺的消旋化工艺 将氨基酸酰胺与具有氨基酸酰胺消旋化酶活性的酶接触。具体而言，本发明涉及一种从氨基酸酰胺中酶解制备光学活性氨基酸的工艺，其方法是使氨基酸酰胺与另外具有 L-或 D-酰胺酶活性的生物催化剂接触。
• Process for the preparation of biocatalysts with previously absent stereoselective enzyme activity
  申请人：DSM N.V.

  公开号：EP0352846A1

  公开（公告）日：1990-01-31

  Process for the preparation of biocatalysts with a previously absent stereoselective enzyme activity, in which a microorganism with a stereoselective enzyme activity is grown in a continuous culture under suitable C- and/or N-limiting conditions, in the presence of a stable substrate with an optical activity for which the microorganism previously lacked stereoselective enzyme activity, until the microorganism uses the substrate, by means of the new stereoselective enzyme activity, as C- and/or N-source to increase the biomass of the continuous culture.

  制备具有以前不具有的立体选择性酶活性的生物催化剂的工艺，在该工艺中，具有立体选择性酶活性的微生物在适当的 C 和/或 N 限制条件下，在具有该微生物以前不具有立体选择性酶活性的光学活性的稳定底物存在下，在连续培养物中生长，直到该微生物通过新的立体选择性酶活性将底物用作 C 和/或 N 源，以增加连续培养物的生物量。
• Process for the preparation of an optically active amino acid amide
  申请人：DSM N.V.

  公开号：EP0442584A1

  公开（公告）日：1991-08-21

  A process for the preparation of optically active amino acid amide whereby a mixture of the L-amino and D-amino acid amides in the presence of 0.5-4 equivalents of an aldehyde, relative to the quantity of amino acid amide, in the presence of a solvent and water, is converted in whole or in part by means of an optically active carboxylic acid into a salt of the amino acid amide and the carboxylic acid, and a portion mainly consisting of one of the diastereoisomers of that salt is separated from the reaction mixture obtained. Instead of a mixture of L-amino and D-amino acid amides it is also possible to use a mixture of the Schiff bases of an amino acid amide and an aldehyde, in which case it is not necessary to add extra aldehyde, and the required quantity of water amounts to at least 1 equivalent relative to the quantity of Schiff base. With this process a high yield of optically active amino acid or the corresponding amino acid is rapidly obtained.

  一种制备光学活性氨基酸酰胺的工艺，在该工艺中，相对于氨基酸酰胺的量，在0.5-4当量的醛的存在下，在溶剂和水的存在下，L-氨基酸酰胺和D-氨基酸酰胺的混合物通过光学活性羧酸全部或部分转化为氨基酸酰胺和羧酸的盐，并从得到的反应混合物中分离出主要由该盐的非对映异构体之一组成的部分。也可以使用氨基酸酰胺和醛的席夫碱混合物来代替 L-氨基酸酰胺和 D-氨基酸酰胺混合物，在这种情况下无需额外添加醛，而且相对于席夫碱的数量，所需的水量至少为 1 个当量。通过这种工艺可以快速获得高产率的光学活性氨基酸或相应的氨基酸。
• 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.
• PROCESS FOR PREPARATION OF ORGANIC CHEMICALS
  申请人：NOVO INDUSTRI A/S

  公开号：EP0330695A1

  公开（公告）日：1989-09-06