4-O-lauroyl sucrose

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 4-O-lauroyl sucrose
• 化学式: C₂₄H₄₄O₁₂
• 分子量: 524.606
• InChiKey: YFTHUKVJRMGIEW-LFXIRSKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  36.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  195.6
• 氢给体数：
  7.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  月桂酸乙烯酯 、 蔗糖 在 subtilisin A from Bacillus licheniformis, lyophilised 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 4-O-lauroyl sucrose 、 mono-1'-O-lauroylsucrose 、 2-O-sucrosyl laurate 、 3-O-lauroyl sucrose 、 4'-O-lauroyl sucrose
  参考文献：
  名称：

  Appearance and distribution of regioisomers in metallo- and serine-protease-catalysed acylation of sucrose in N,N-dimethylformamide

  摘要：

  The appearance and distribution of monoester regioisomers were investigated in the virtually irreversible acylation of sucrose with the enol ester, vinyl laurate, as acyl donor catalysed by serine proteases and a metalloprotease in the hydrophilic, aprotic solvent N,N-dimethylformamide. Sucrose laurate was obtained in yields from 12 to 53% after 48 h under different catalytic conditions. The serine protease ALP-901, derived from a Streptomyces sp., produced the highest yield at this reaction time, while reaction with the zinc-protease thermolysin achieved the overall highest yield (63%) after 6 h, with only monoesters synthesised. The total conversion of sucrose after 48 h ranged from 19 to 96%. The highest degree of conversion was observed in the reaction with thermolysin, while the reactions without protein and with ALP-901 resulted in 82% and 66% sucrose conversion, respectively. 2-O-Lauroyl sucrose was the most abundant monoester regioisomer synthesised and the highest concentration observed was 23.7 mM after 24h in the thermolysin-catalysed reaction. The highest concentration of 2-O-lauroyl sucrose detected in the reaction catalysed by ALP-901 was 19.0 mM, while it was 17.0 mM the reaction without protein, both after 48 h. The detected appearance of the sucrose laurate regioisomers largely corresponded to the apparent rates of formation, and 2-O-lauroyl sucrose was among the first regioisomers to appear in all reactions. The observed sucrose laurate regioisomeric distribution after 48 h (2:3:4:6:1':3') was 72:5:2:1:7:14 in the reaction catalysed by ALP-901, and 74:5:2:1:7:13 in the reaction without protein. In the reaction catalysed by thermolysin the distribution was 71:5:2:-:9:13 after 6 h and 86:8:-:-:4:3 after 48 h of reaction. The esterification of sucrose with vinyl laurate without protein in the reaction mixture appeared to be catalysed in the presence of aluminosilicate molecular sieves. Non-catalytic protein in the reaction medium seemed to lower the catalytic activity of the molecular sieves. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.04.017

文献信息

• Appearance and distribution of regioisomers in metallo- and serine-protease-catalysed acylation of sucrose in N,N-dimethylformamide
  作者：Aleksander Lie、Anne S. Meyer、Lars Haastrup Pedersen

  DOI：10.1016/j.molcatb.2014.04.017

  日期：2014.8

  The appearance and distribution of monoester regioisomers were investigated in the virtually irreversible acylation of sucrose with the enol ester, vinyl laurate, as acyl donor catalysed by serine proteases and a metalloprotease in the hydrophilic, aprotic solvent N,N-dimethylformamide. Sucrose laurate was obtained in yields from 12 to 53% after 48 h under different catalytic conditions. The serine protease ALP-901, derived from a Streptomyces sp., produced the highest yield at this reaction time, while reaction with the zinc-protease thermolysin achieved the overall highest yield (63%) after 6 h, with only monoesters synthesised. The total conversion of sucrose after 48 h ranged from 19 to 96%. The highest degree of conversion was observed in the reaction with thermolysin, while the reactions without protein and with ALP-901 resulted in 82% and 66% sucrose conversion, respectively. 2-O-Lauroyl sucrose was the most abundant monoester regioisomer synthesised and the highest concentration observed was 23.7 mM after 24h in the thermolysin-catalysed reaction. The highest concentration of 2-O-lauroyl sucrose detected in the reaction catalysed by ALP-901 was 19.0 mM, while it was 17.0 mM the reaction without protein, both after 48 h. The detected appearance of the sucrose laurate regioisomers largely corresponded to the apparent rates of formation, and 2-O-lauroyl sucrose was among the first regioisomers to appear in all reactions. The observed sucrose laurate regioisomeric distribution after 48 h (2:3:4:6:1':3') was 72:5:2:1:7:14 in the reaction catalysed by ALP-901, and 74:5:2:1:7:13 in the reaction without protein. In the reaction catalysed by thermolysin the distribution was 71:5:2:-:9:13 after 6 h and 86:8:-:-:4:3 after 48 h of reaction. The esterification of sucrose with vinyl laurate without protein in the reaction mixture appeared to be catalysed in the presence of aluminosilicate molecular sieves. Non-catalytic protein in the reaction medium seemed to lower the catalytic activity of the molecular sieves. (C) 2014 Elsevier B.V. All rights reserved.