Chemoenzymatic synthesis of enantiomerically enriched α-hydroxyamides |
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Authors: | Wiktor Szymanski Ryszard Ostaszewski |
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Institution: | aFaculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland;bInstitute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01–224 Warsaw, Poland |
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Abstract: | A study on a chemoenzymatic synthesis of model α-hydroxyamide was performed. Special attention was paid to the optimization of the enzymatic process, both on the selection of enzyme and cosolvent. An intriguing influence of cosolvent on the enantioselectivity of Wheat Germ Lipase and Amano PS Lipase catalyzed hydrolysis was observed, as the results obtained proved that enzyme's enantioselectivity is directly correlated with cosolvent's hydrophobicity. In the best example (Wheat Germ lipase, Et2O used as a cosolvent), the reaction proceeded with E = 55, and the target compound was obtained in 33% yield with 92.7%ee. |
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Keywords: | α -Hydroxyamides Passerini reaction Lipases Enantioselectivity Cosolvent effect |
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