کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
69815 | 48794 | 2013 | 6 صفحه PDF | دانلود رایگان |

• 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.
Figure optionsDownload as PowerPoint slide
Journal: Journal of Molecular Catalysis B: Enzymatic - Volume 98, 30 December 2013, Pages 92–97