(6R)-3-acetoxymethyl-8-oxo-7t-pentanoylamino-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 3595-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (6R)-3-acetoxymethyl-8-oxo-7t-pentanoylamino-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 英文别名: 7-Pentanoylamino-cephalosporadesinsaeure；(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-(pentanoylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS: 3595-18-4
• 化学式: C₁₅H₂₀N₂O₆S
• 分子量: 356.4
• InChiKey: YDAIQQDPAPDNAB-BXUZGUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (6R)-3-acetoxymethyl-8-oxo-7t-pentanoylamino-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 在 recombinant VAC enzyme 作用下， 反应 0.17h， 生成 7-氨基头孢烷酸
  参考文献：
  名称：

  On the substrate preference of glutaryl acylases

  摘要：

  The substrate preferences of three acylases two wild-type enzymes and an evolved variant obtained by directed evolution - which are prototypical enzymes for glutaryl-7-ACA acylase and cephalosporin C acylase subfamilies, have been investigated. A preliminary screening of enzymes' performances on a large set of substrates has been carried out by a colorimetric assay performed in 96-well plates and by a pH-Star monitoring the hydrolytic activities. Subsequently, kinetic data for selected substrates have been determined, thus elucidating the substrate preference of members of glutaryl-7-ACA acylase vs. cephalosporin C acylase subfamilies. These achievements pave the way to the ability of choosing the best enzyme for the hydrolysis of different compounds of industrial importance. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.001
• 作为产物：
  描述：

  戊酸酐 、 7-氨基头孢烷酸 在 碳酸氢钠 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (6R)-3-acetoxymethyl-8-oxo-7t-pentanoylamino-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  On the substrate preference of glutaryl acylases

  摘要：

  The substrate preferences of three acylases two wild-type enzymes and an evolved variant obtained by directed evolution - which are prototypical enzymes for glutaryl-7-ACA acylase and cephalosporin C acylase subfamilies, have been investigated. A preliminary screening of enzymes' performances on a large set of substrates has been carried out by a colorimetric assay performed in 96-well plates and by a pH-Star monitoring the hydrolytic activities. Subsequently, kinetic data for selected substrates have been determined, thus elucidating the substrate preference of members of glutaryl-7-ACA acylase vs. cephalosporin C acylase subfamilies. These achievements pave the way to the ability of choosing the best enzyme for the hydrolysis of different compounds of industrial importance. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.12.001

文献信息

• Processes using amino acid dehydrogenases and ketoreductase-based cofactor regenerating system
  申请人：Codexis, Inc.

  公开号：US10196667B2

  公开（公告）日：2019-02-05

  The present disclosure relates to the use of an amino acid dehydrogenase in combination with a cofactor regenerating system comprising a ketoreductase. In particular embodiments, the process can be used to prepare L-tert-leucine using a leucine dehydrogenase.

  本公开涉及将氨基酸脱氢酶与由酮还原酶组成的辅助因子再生系统结合使用。在具体的实施方案中，该工艺可用于使用亮氨酸脱氢酶制备 L-叔亮氨酸。
• 922. Cephalosporanic acids. Part II. Displacement of the acetoxy-group by nucleophiles
  作者：J. D. Cocker、B. R. Cowley、J. S. G. Cox、S. Eardley、G. I. Gregory、J. K. Lazenby、A. G. Long、J. C. P. Sly、G. A. Somerfield

  DOI：10.1039/jr9650005015

  日期：——
• Kinetic resolutions of racemic amines and alcohols catalyzed by an industrial glutaryl-7-aminocephalosporanic acid acylase with unexpected broad substrate specificity
  作者：Stefano Raimondi、Luca Forti、Daniela Monti、Sergio Riva

  DOI：10.1016/s0957-4166(03)00171-x

  日期：2003.5

  An industrial glutaryl-7-aminocephalosporanic acid acylase (GAR) possesses a significant broad substrate specificity that crosses over the usual cephalosporanic skeleton. Enantioselective amidase and even esterase activities have been observed with all the glutarates of racemic substrates investigated, with a stereopreference for the (S)-enantiomer. The different physical-chemical properties of reagents and products allow their easy separation by solvent extraction, avoiding cumbersome chromatography or distillation processes during reaction work-up. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Processes Using Amino Acid Dehydrogenases and Ketoreductase-Based Cofactor Regenerating System
  申请人：Cabirol Fabien L.

  公开号：US20130029385A1

  公开（公告）日：2013-01-31

  The present disclosure relates to the use of an amino acid dehydrogenase in combination with a cofactor regenerating system comprising a ketoreductase. In particular embodiments, the process can be used to prepare L-tert-leucine using a leucine dehydrogenase.
• PROCESSES USING AMINO ACID DEHYDROGENASES AND KETOREDUCTASE-BASED COFACTOR REGENERATING SYSTEM
  申请人：Codexis, Inc.

  公开号：US20150284749A1

  公开（公告）日：2015-10-08

  The present disclosure relates to the use of an amino acid dehydrogenase in combination with a cofactor regenerating system comprising a ketoreductase. In particular embodiments, the process can be used to prepare L-tert-leucine using a leucine dehydrogenase.