Aureobasidium pullulans as a key for the preparation of optical purity (R)-2-(anthracen-9-yl)-2-methoxyacetic acid - The chiral auxiliary reagent in determination of absolute configuration

摘要

Optically pure (R)-2-(anthracen-9-yl)-2-methoxyacetic acid.((R)-9-AMA) was obtained. The most important stage of the synthesis generating chirality and ensuring high enantioselectivity was the stage of desymmetrization of prochiral alpha-ketoester. Enzymatic biotransformation was used in the presence of Saccharomyces cerevisiae and Aureobasidium pullulans. Biotransformation using S. cerevisiae leads to 65-70% enantiomeric excess (R-isomer). The antimycotic agent Boni Protect containing live cells of A. pullulans allowed to obtain enantiomerically pure (R)-9-AMA. (C) 2015 Elsevier B.V. All rights reserved.