Enantioselective production of benzoin from benzoin acetate via kinetic resolution and deracemization using Rhizopus oryzae.
In this study, the production of enantiopure benzoin from rac-benzoin acetate was achieved by lipase catalyzed kinetic resolution combined with deracemization using Rhizopus oryzae (CBS111718). The growth cells were pretreated with 20 kHz and 30 kHz ultrasound irradiation and mechanical homogenization. Approximately 100% conversion and 96% enantiomeric excess of the product (S-benzoin) were obtained by applying 20 kHz ultrasound irradiation at pH 6. The deracemization process involves new and important processes that allow for the transformation of a racemate into a single stereoisomeric product in 100% theoretical yields. Moreover, the application of ultrasound increases the conversion rate by reducing mass transfer limitation.
Songür
Rahime
R
Ankara University, Faculty of Engineering, Department of Chemical Engineering, Ankara, Turkey.
Lurçi
Binnaz
B
Bayraktar
Emine
E
Mehmetoğlu
Ulkü
U
Demir
Ayhan S
AS
D000085:Acetates / Q000737:chemistry; D001573:Benzoin / Q000138:chemical synthesis*; D002384:Catalysis / Q000528:radiation effects; D006868:Hydrolysis / Q000187:drug effects / Q000528:radiation effects; D007536:Isomerism; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D010940:Plant Proteins / Q000378:metabolism*; D019998:Racemases and Epimerases / Q000378:metabolism*; D011846:Radio Waves; D012233:Rhizopus / Q000201:enzymology / Q000528:radiation effects*; D013237:Stereoisomerism
D000085:Acetates; D010940:Plant Proteins; D008049:Lipase; D019998:Racemases and Epimerases; D001573:Benzoin