ENZYMATIC MONOACYLATION OF FRUCTOSE BY 2 PROCEDURES

被引:62
作者
SCHECKERMANN, C
SCHLOTTERBECK, A
SCHMIDT, M
WRAY, V
LANG, S
机构
[1] TECH UNIV CAROLO WILHELMINA BRAUNSCHWEIG, INST BIOCHEM & BIOTECHNOL, D-38106 BRAUNSCHWEIG, GERMANY
[2] UNILEVER RES LABS VLAARDINGEN, 3130 AC VLAARDINGEN, NETHERLANDS
[3] GESELL BIOTECHNOL FORSCH MBH, W-3300 BRAUNSCHWEIG, GERMANY
关键词
FRUCTOSE FATTY ACID ESTERS; LIPASE; SYNTHESIS IN ORGANIC SOLVENTS; PHENYLBORONIC ACID;
D O I
10.1016/0141-0229(94)00005-C
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Two methods for the lipase-catalyzed monoacylation of fructose with long-chain fatty acids (e.g., palmitic, stearic) in hexane or 2-methyl-2-butanol are described. Using method A the enzymatic monoacylation of fructose was carried out at a molar ratio up to 15:1 of fatty acid to fructose in 2-methyl-2-butanol at 55 degrees C using Lipozyme(TM). The reaction of method B using Lipozyme(TM) or the lipase of Candida antarctica in n-hexane at 60 degrees C was favored by a 1:3:4.5 molar ratio of fatty acid to fructose to phenylboronic acid; phenylboronic acid served as a solubilizing agent for the sugar in hexane. Method A gave a mixture of the C-1 and C-6 monoacylated fructose fatty acid esters, whereas for method B only the C-1 monoester was found. In each case pyranose and furanose isomeric forms of the sugar were apparent in solution. Typically, yields of about 40% were obtained. Adding fructose fatty acid esters to water lowered the surface tension from 72 to a minimum of 27 mN m(-1) at critical micelle concentrations of 10(-5) to 10(-3) mol l(-1) at 37 degrees C.
引用
收藏
页码:157 / 162
页数:6
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