کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
69815 48794 2013 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis
موضوعات مرتبط
مهندسی و علوم پایه مهندسی شیمی کاتالیزور
پیش نمایش صفحه اول مقاله
Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis
چکیده انگلیسی


• The CAL-B-catalyzed enantioselective acylation of hydroxy esters has been demonstrated to be accompanied by hydrolysis.
• The possibility of enzymatic hydrolysis needs to be carefully investigated.
• When the acyl donor was used in a higher excess, the hydrolysis could be suppressed.
• Enantiomerically enriched β-hydroxy acids were prepared through CAL-B-catalyzed hydrolysis.

The ester function of ethyl cis-(±)-2-hydroxycyclopentane-1-carboxylate [(±)-1] and ethyl (±)-5-hydroxycyclopent-1-enecarboxylate [(±)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E > 200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30 °C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee = 90%) and 5-hydroxycyclopent-1-enecarboxylic acid (ee = 47%) were prepared through de novo CAL-B-catalyzed hydrolysis of (±)-1 and (±)-2 with added H2O in t-BuOMe at 30 °C.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Catalysis B: Enzymatic - Volume 98, 30 December 2013, Pages 92–97
نویسندگان
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