Thiol-functionalization of acrylic ester monomers catalyzed by immobilized Humicola insolens cutinase

详细信息	查看全文 | 推荐本文 |

• 作者：Christian Kazenwadel^a ; Sabine Eiben^a ; Steffen Maurer^b ; Holger Beuttler^a ; Dennis Wetzl^a ; Bernhard Hauer^a ; Katja Koschorreck^a ; ^c ; ^{katja.koschorreck@uni-duesseldorf.de}
• 关键词：Cutinase ; Humicola insolens ; Functional monomers ; Immobilization ; Methyl acrylate ; Transesterification
• 刊名：Enzyme and Microbial Technology
• 出版年：2012
• 期刊代码：26_01410229
• 类别：ce
• 出版时间：10 June, 2012
• 卷：51
• 期：1
• 页码：9-15
• 文件大小：428 K

摘要

Immobilized cutinase HiC from the ascomycete Humicola insolens was applied as a novel biocatalyst for the synthesis of functionalized acryclic esters by transesterification. As a model reaction, transesterification of methyl acrylate with 6-mercapto-1-hexanol at a high molar ratio in a solvent free system was chosen. Besides two minor Michael-addition by-products, 6-mercaptohexyl acrylic ester was identified as the main product with the thiol as the functional end group. Reaction conditions were optimized regarding the influence of water (0-1.72 M), temperature (22-50 掳C), product inhibition and addition of the radical inhibitor butylated hydroxytoluol (BHT; 0.14-0.71 M) on conversion and by-product formation. Highest conversion of 6-mercapto-1-hexanol to 6-mercaptohexyl acrylic ester (95.4 卤 0.3%) was achieved after 6 h at 40 掳C in the presence of 0.025%(w/w) water without formation of by-products in a solvent free system. Applying methyl methacrylate, transesterification with 6-mercapto-1-hexanol was significantly lower (43.6 卤 0.1%) compared to transesterification of methyl acrylate with 6-mercapto-1-hexanol.