A parametric study on biphasic medium conditions for the enantioselective production of Naproxen by Candida rugosa lipase

Takac S., Mutlu D.

APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, cilt.141, sa.1, ss.15-26, 2007 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 141 Sayı: 1
  • Basım Tarihi: 2007
  • Doi Numarası: 10.1007/s12010-007-9207-3
  • Dergi Adı: APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.15-26
  • Anahtar Kelimeler: biphasic systems, Candida rugosa lipase, enantioselectivity, Naproxen methyl ester, S-Naproxen, KINETIC RESOLUTION, ENZYMATIC RESOLUTION, ORGANIC-SOLVENTS, RACEMIC NAPROXEN, CONTINUOUS REACTOR, METHYL-ESTER, HYDROLYSIS, WATER, PH, (S)-(+)-NAPROXEN
  • Ankara Üniversitesi Adresli: Evet

Özet

A parametric study to increase the enantioselectivity of Candida rugosa lipase (CRL) toward S-Naproxen production by the hydrolysis of racemic Naproxen methyl ester in an aqueous-organic biphasic batch system was carried out. Effects of organic solvent type, aqueous phase/organic solvent volume ratio, agitation rate, concentrations of the substrate and the enzyme, pH of the aqueous phase, and temperature on the enantiomeric excess for the product (ee(p)), on the enantiomeric ratio (E) and on the conversion (x) were evaluated. Employing isooctane as the solvent resulted in higher ee(P), E, and x than those obtained in hexane, cyclohexane, and toluene. The higher volume ratio of aqueous phase/organic solvent employed, the higher the conversion and enantioselectivity achieved. The increase in agitation rate increased the hydrolysis rate. Higher concentration of racemic Naproxen methyl ester than 10 mg/mL decreased both the conversion and enantioselectivity. The increase in crude CRL concentration resulted in enhancement of x, but the decrease of ee(P) and E. Acidic pH led to higher conversion and enantioselectivity than the medium and alkaline pH values. A further increase in temperature to over 45 degrees C decreased the conversion and enantioselectivity. The highest enantiomeric ratio achieved in the S-Naproxen production was E = 171.1, with x = 49.8%, and ee(P) = 95.7%.