2-butyl ferulate | 909104-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-butyl ferulate
• 英文别名: butan-2-yl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 909104-79-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: LWGTYKIOSJFSSX-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-butyl ferulate 在 Sporotrichum thermophile type C feruloyl esterase 、 水 作用下， 生成 阿魏酸
  参考文献：
  名称：

  Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates

  摘要：

  The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series Of C-1-C-4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the K-m values of 1.64-0.51 and 0.19-0.1, respectively. Comparison of k(cat), and k(cat)/K-m values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to L-arabinose, using as a reaction system a ternary water-organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as D-arabinose, D-glucose, D-xylose, D-Mannose, D-fructose, D-galactose, D-ribose and model substrates such as 4-nitrophenyl alpha-L-arabinofuranoside and 4-nitrophenyl alpha-L-arabinopyranoside. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.037
• 作为产物：
  描述：

  ethyl 4-hydroxy-3-methoxycinnamate 在 Sporotrichum thermophile type C feruloyl esterase 、 水 、 乙酰氯 作用下， 反应 16.0h， 生成 2-butyl ferulate
  参考文献：
  名称：

  Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates

  摘要：

  The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series Of C-1-C-4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the K-m values of 1.64-0.51 and 0.19-0.1, respectively. Comparison of k(cat), and k(cat)/K-m values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to L-arabinose, using as a reaction system a ternary water-organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as D-arabinose, D-glucose, D-xylose, D-Mannose, D-fructose, D-galactose, D-ribose and model substrates such as 4-nitrophenyl alpha-L-arabinofuranoside and 4-nitrophenyl alpha-L-arabinopyranoside. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.037

文献信息

• Regioselective esterase-catalyzed feruloylation of l-arabinobiose
  作者：Christina Vafiadi、Evangelos Topakas、Paul Christakopoulos

  DOI：10.1016/j.carres.2006.05.022

  日期：2006.9

  The regioselective chemoenzymatic synthesis of O-[5-O-(trans-feruloyl)-alpha-L-arabinofuranosyl]-(1 -> 5)-L-arabinofuranose has been achieved. The reaction parameters affecting the feruloylation rate and conversion of the enzymatic synthesis, such as the composition of the reaction medium, substrate and enzyme concentration, have been investigated. (c) 2006 Elsevier Ltd. All rights reserved.
• Mapping the hydrolytic and synthetic selectivity of a type C feruloyl esterase (StFaeC) from Sporotrichum thermophile using alkyl ferulates
  作者：Christina Vafiadi、Evangelos Topakas、Ken K.Y. Wong、Ian D. Suckling、Paul Christakopoulos

  DOI：10.1016/j.tetasy.2004.11.037

  日期：2005.1

  The active site of Sporotrichum thermophile type C feruloyl esterase (StFaeC) was probed using a series Of C-1-C-4 alkyl ferulates. The affinities for straight and branched alkyl ferulates were demonstrated by the K-m values of 1.64-0.51 and 0.19-0.1, respectively. Comparison of k(cat), and k(cat)/K-m values shows that the enzyme hydrolyzed n-propyl ferulate faster and iso-propyl ferulate more efficiently. Alkyl ferulates were applied also for substrate selectivity mapping of feruloyl esterase to catalyze feruloyl group transfer to L-arabinose, using as a reaction system a ternary water-organic mixture consisting of n-hexane, t-butanol and water. Lengthening the aliphatic side chain was the most significant factor causing lower synthetic activity of the enzyme. The reaction parameters affecting the feruloylation rate and the conversion of the enzymatic process, such as the temperature and substrate concentration have been investigated. Under identical reaction conditions, the enzyme feruloylated other monosaccharides such as D-arabinose, D-glucose, D-xylose, D-Mannose, D-fructose, D-galactose, D-ribose and model substrates such as 4-nitrophenyl alpha-L-arabinofuranoside and 4-nitrophenyl alpha-L-arabinopyranoside. (C) 2004 Elsevier Ltd. All rights reserved.