Enantioselective Production of Benzoin from Benzoin Acetate via Kinetic Resolution and Deracemization using Rhizopus oryzae

SONGÜR R., Lurci B., BAYRAKTAR E., Mehmetoglu U., DEMİR A. G.

ARTIFICIAL CELLS BLOOD SUBSTITUTES AND BIOTECHNOLOGY, cilt.39, sa.3, ss.162-168, 2011 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 39 Sayı: 3
  • Basım Tarihi: 2011
  • Doi Numarası: 10.3109/10731199.2010.516261
  • Dergi Adı: ARTIFICIAL CELLS BLOOD SUBSTITUTES AND BIOTECHNOLOGY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.162-168
  • Anahtar Kelimeler: alpha-hydroxy ketone, benzoin, deracemization, ultrasound, hydrolysis, Rhizopus oryzae, ALPHA-HYDROXY KETONES, SOLVENT-FREE SYSTEM, DERACEMISATION, DECARBOXYLASE, HYDROLYSIS, ACID
  • Ankara Üniversitesi Adresli: Evet

Özet

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.