The effects of ultrasonication and reaction parameters on the biocatalytic deracemization of racemic propranolol

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SONGÜR R., Mehmetoglu U.

JOURNAL OF THE FACULTY OF ENGINEERING AND ARCHITECTURE OF GAZI UNIVERSITY, vol.33, no.2, pp.559-566, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 33 Issue: 2
  • Publication Date: 2018
  • Doi Number: 10.17341/gazimmfd.416366
  • Journal Name: JOURNAL OF THE FACULTY OF ENGINEERING AND ARCHITECTURE OF GAZI UNIVERSITY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.559-566
  • Keywords: Biocatalytic deracemization, propranolol, beta-blocker, enantioselectivity, Rhizopus oryzae, BETA-BLOCKERS, CHEMOENZYMATIC SYNTHESIS, BUILDING-BLOCKS, (S)-PROPRANOLOL, BIOTRANSFORMATIONS, SEPARATION, RESOLUTION
  • Ankara University Affiliated: Yes

Abstract

Pharmaceutically important beta-blockers, which are especially used for treatment of cardiovasculer disease, are chiral. The enantiomers of beta-blocker have different pharmacokinetic and pharmacodynamic properties. For this reason, it is important that enantiomers of beta-blocker should use separately. In this study, the production of enantiomerically pure propranolol, which has commonly use as beta-blockers, was aimed. In accordance with this purpose, the production of enantiomerically pure propranolol via biocatalytic deracemization using Rhizopus oryzae CBS 111718 was investigated. The effect of different parameters to the reaction (cell disruption methods, substrate concentration, pH of reaction medium, reaction time, etc.) using R. oryzae was investigated to determine optimum conditions. At the end of all this experiments, the highest enantiomeric excess (ee%) and conversion (C%) values were obtained as ee%=28.4 and C%=60.2 at pH 7 phosphate buffer, 3 mM substrate concentration, 10 min duration of ultrasonication, 6 days reaction time.