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

• Published in: Journal of molecular catalysis. B, Enzymatic Enzymatic, 2015-11, Vol.121, p.28-31
• Main Authors: Kołodziejska, Renata, Wróblewski, Marcin, Studzińska, Renata, Karczmarska-Wódzka, Aleksandra, Grela, Izabela, Augustyńska, Beata, Modzelewska-Banachiewicz, Bożena
• Format: Article
• Language: English
• Subjects: 2-(Anthracen-9-yl)-2-methoxyacetic acid; Aureobasidium pullulans; Microbiological reduction; Saccharomyces cerevisiae; Stereochemistry
• ISSN: 1381-1177; 1873-3158
• DOI: 10.1016/j.molcatb.2015.05.007

•(R)-2-(anthracen-9-yl)-2-methoxyacetic acid was obtained using the reduction α-ketoester.•Enzymatic reduction was carried out using Saccharomyces cerevisiae and Aureobasidium pullulans.•Antimycotic agent Boni Protect containing live A. pullulans cells is the best catalyst. 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 α-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.