李智斌,黄晓凯,胡巧红.化学通报,2015,78(7):659-662.
脂肪酶Lipozyme 435催化合成海藻糖脂肪酸单酯
Synthesis of Monoacyl Trehaloses catalyzed by Lipozyme 435
投稿时间:2015-01-15  修订日期:2015-03-11
DOI:
中文关键词:  Lipozyme 435  海藻糖脂肪酸单酯  增溶
英文关键词:Lipozyme 435  monoacyl trehaloses  solubilization
基金项目:
作者单位E-mail
李智斌 广东药学院药科学院药剂系 syaoranlee@foxmail.com 
黄晓凯 广东药学院药科学院药剂系  
胡巧红* 广东药学院药科学院药剂系 hu_qiaohong@163.com 
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中文摘要:
      本文通过脂肪酶催化高选择性地合成海藻糖脂肪酸单酯,以期获得具有优良增溶性能的新型非离子型表面活性剂。以脂肪酶Lipozyme 435为催化剂,将海藻糖与脂肪酸反应合成海藻糖脂肪酸单酯,应用薄层色谱法监测反应,筛选反应体系的溶剂,再用柱层析方法对产物进行分离纯化。应用FT-IR和1H-NMR确证产物结构,测定产物溶解性能,并以芘荧光探针法测定产物的临界胶束浓度(CMC)。结果表明,以脂肪酶Lipozyme 435为催化剂,叔丁醇/吡啶为溶剂,酯化反应可顺利进行。FT-IR和1H-NMR图谱说明该反应可高选择性地合成海藻糖脂肪酸单酯。海藻糖脂肪酸单酯的溶解性能和临界胶束浓度均随着脂肪链长度的增加而降低。通过综合考虑溶解性能和CMC,有望获得合适的海藻糖脂肪酸单酯作为潜在的增溶剂。
英文摘要:
      As novel non-ionic surfactants with good solubilization properties, monoacyl trehaloses were synthesized by lipase catalyst. Using Lipozyme 435 as catalyst, monoacyl trehaloses were synthesized by reaction of trehalose and fatty acid. The reaction solvent was optimized under the monitoring of reaction solution by thin layer chromatography (TLC). The products were purified through column chromatography to obtain monoacyl trehaloses. FT-IR and 1H-NMR were used to confirm the chemical structure of monoacyl trehaloses. The solubility and critical micelle concentration (CMC) of monoacyl trehaloses were determined. Trehalose successfully reacted with fatty acid in tert-butanol/pyridine(3:2, v/v) with Lipozyme 435 as catalyst. FT-IR and 1H-NMR spectrum showed that this reaction selectively produced monoacyl trehaloses. The solubility and CMC of monoacyl trehaloses decreased with the increase of aliphatic chain length. By considering the solubility and CMC, it is expected to obtain suitable monoacyl trehalose as a novel solubilizer.
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