(R)-2-Hydroxy-butyric acid butyl ester | 928835-95-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-Hydroxy-butyric acid butyl ester
• 英文别名: Butyl (2R)-2-hydroxybutanoate
• CAS: 928835-95-4
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: YFFBWGUXPFAXRS-SSDOTTSWSA-N

物化性质

• 沸点：
  204.6±8.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  DL-2-羟基丁酸 、 正丁醇 在 磷脂酶B 作用下， 以 环己烷 为溶剂， 生成 (S)-2-羟基丁酸正丁酯 、 (R)-2-Hydroxy-butyric acid butyl ester
  参考文献：
  名称：

  Tailoring lipase specificity by solvent and substrate chemistries

  摘要：

  An acyl binding structural model has been developed to explain the observed catalytic efficiencies and enantioselectivities of Candida rugosa lipase-catalyzed (trans)esterification reactions involving 2-hydroxy acids and vinyl esters, respectively, and acylation reactions involving both cyclic and acyclic alcohols. A clear minimum was observed for (trans)esterification of six-carbon acyl moieties. Morever, the stereoselectivity of 2-hydroxy acid esterification in a number of hydrophilic and hydrophobic solvents was dependent on the acyl chain length: S-isomers of 2-hydroxy acids were acylated for acyl chain lengths of six or fewer, whereas the R-isomers were preferentially esterified for acyl chain lengths of eight or more. These results suggest that CRL contains both large and small acyl binding regions or pockets with high catalysis observed for proper fitting substrates into either pocket. CRL is also highly selective and reactive on secondary cyclic alcohols. In particular, the R isomers of menthol and sec-phenethanol are acylated efficiently by straight-chain vinyl esters. The catalytic efficiency of acylation (i.e., V(max)/K(m) for the secondary alcohol) is strongly dependent on the acyl chain length. Once again, a clear minimum is observed with vinyl caproate (C6) as acyl donor. This phenomenon may reflect the greater degree of steric hinderance in the acyl enzyme intermediate caused by the caproate group. A mechanistic and thermodynamic rationale was proposed for the effects of solvent and substrate chemistries on CRL catalysis in organic solvents.

  DOI：

  10.1021/jo00064a008

文献信息

• US6610730B2
  申请人：——

  公开号：US6610730B2

  公开（公告）日：2003-08-26
• Tailoring lipase specificity by solvent and substrate chemistries
  作者：Sanghamitra Parida、Jonathan S. Dordick

  DOI：10.1021/jo00064a008

  日期：1993.6

  An acyl binding structural model has been developed to explain the observed catalytic efficiencies and enantioselectivities of Candida rugosa lipase-catalyzed (trans)esterification reactions involving 2-hydroxy acids and vinyl esters, respectively, and acylation reactions involving both cyclic and acyclic alcohols. A clear minimum was observed for (trans)esterification of six-carbon acyl moieties. Morever, the stereoselectivity of 2-hydroxy acid esterification in a number of hydrophilic and hydrophobic solvents was dependent on the acyl chain length: S-isomers of 2-hydroxy acids were acylated for acyl chain lengths of six or fewer, whereas the R-isomers were preferentially esterified for acyl chain lengths of eight or more. These results suggest that CRL contains both large and small acyl binding regions or pockets with high catalysis observed for proper fitting substrates into either pocket. CRL is also highly selective and reactive on secondary cyclic alcohols. In particular, the R isomers of menthol and sec-phenethanol are acylated efficiently by straight-chain vinyl esters. The catalytic efficiency of acylation (i.e., V(max)/K(m) for the secondary alcohol) is strongly dependent on the acyl chain length. Once again, a clear minimum is observed with vinyl caproate (C6) as acyl donor. This phenomenon may reflect the greater degree of steric hinderance in the acyl enzyme intermediate caused by the caproate group. A mechanistic and thermodynamic rationale was proposed for the effects of solvent and substrate chemistries on CRL catalysis in organic solvents.