6-lauroyl-β-D-fructofuranose | 20881-10-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-lauroyl-β-D-fructofuranose
• 英文别名: 6-O-Lauroyl-D-fructofuranose；[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl dodecanoate
• CAS: 20881-10-1
• 化学式: C₁₈H₃₄O₇
• 分子量: 362.464
• InChiKey: OCEOFTSKSVEBGY-NRSFXHEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  月桂酸 、 果糖 在 Candida antarctica lipase B 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 生成 1-lauroyl-β-D-fructofuranose 、 1,6-dilauroyl-β-D-fructofuranose 、 6-lauroyl-β-D-fructofuranose 、 1,6-dilauroyl-α-D-fructofuranose 、 1-lauroyl-β-D-fructopyranose 、 6-lauroyl-α-D-fructofuranose
  参考文献：
  名称：

  Efficient mono-acylation of fructose by lipase-catalyzed esterification in ionic liquid co-solvents

  摘要：

  Fructose monoesters are eco-friendly nonionic surfactants in various applications. Selective preparation of mono-acylated fructose is challenging due to the multiple hydroxyl sites available for acylation both chemically and enzymatically. Ionic liquids (ILs) have profound impacts not only on the reaction media but also on the catalytic properties of enzymes in the acylation process. In this study, utilizing an IL co-solvent system, selective synthesis of mono-acylated fructose with lauric acid catalyzed by immobilized Candida antarctica lipase B (CALB) was investigated. The imidazolium-based ILs selected as co-solvents with 2-methyl-2-butanol (2M2B) markedly improved the ratios of monolauroyl fructose in the presence of 60% [BMIM][TfO] (v/v) and 20% [BMIM][BF4] (v/v), in which the mono-acylated fructose was 85% and 78% respectively. Based on a Ping-Pong Bi-Bi model, a kinetic equation was fitted, by which the kinetic parameters revealed that the affinity between fructose and acyl-enzyme intermediate was enhanced. The inhibition effect of fructose on free enzyme was weakened in the presence of IL co-solvents. The conformation of CALB binding substrates also changed in the co-solvent system as demonstrated by Fourier transform infrared spectra. These results demonstrated that the variation of CALB kinetic characteristics was a crucial factor for the selectivity of mono-acylation in ILs/2M2B co-solvents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.08.009