Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst

In this study, enantiomerically pure (S)-1-phenylethanol was produced via asymmetric bioreduction of acetophenone. Ispir bean (Phaseolus vulgaris) was used as an alcohol dehydrogenase (ADH) source since whole cells are cheaper than isolated enzymes. Acetone powder methodology was applied for biocata...

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Main Authors:	Atak Gunay Baydar, Bayraktar Emine, Mehmetoglu Ülkü
Format:	Article
Language:	English
Published:	De Gruyter 2019-01-01
Series:	Green Processing and Synthesis
Subjects:	(s)-1-phenylethanol response surface methodology asymmetric bioreduction acetone powder enantioselectivity
Online Access:	https://doi.org/10.1515/gps-2019-0021

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record_format	Article
spelling	doaj-34cffd8c2d5f40cb988b6688e29c79192021-10-02T19:09:36ZengDe GruyterGreen Processing and Synthesis2191-95502019-01-018152553210.1515/gps-2019-0021gps-2019-0021Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalystAtak Gunay Baydar0Bayraktar Emine1Mehmetoglu Ülkü2Ankara University, Faculty of Engineering, Department of Chemical Engineering, 06100, Tandogan, Ankara, TurkeyAnkara University, Faculty of Engineering, Department of Chemical Engineering, 06100, Tandogan, Ankara, TurkeyAnkara University, Faculty of Engineering, Department of Chemical Engineering, 06100, Tandogan, Ankara, TurkeyIn this study, enantiomerically pure (S)-1-phenylethanol was produced via asymmetric bioreduction of acetophenone. Ispir bean (Phaseolus vulgaris) was used as an alcohol dehydrogenase (ADH) source since whole cells are cheaper than isolated enzymes. Acetone powder methodology was applied for biocatalyst. Glucose was used as a cosubstrate in-order to regenerate cofactor (NADPH). The reactions were carried out in an orbital shaker whose temperature and agitation rate can be controlled. (S)-1-phenylethanol concentration was analyzed by HPLC using a Chiralcel OB column. Effects of the reaction time, substrate concentration, cosubstrate concentration and biocatalyst concentration on the (S)-1-phenylethanol production were investigated using Response Surface Methodology (RSM). 36 h bioreduction time, 6 mM acetophenone concentration, 25.15 mM glucose concentration, and 175 mg/mL biocatalyst concentration were determined as optimum values. In these conditions, 2.4 mM (S)-1-phenylethanol was obtained in phosphate buffer (pH=7.0) at 30°C with >99% enantiomeric excess.https://doi.org/10.1515/gps-2019-0021(s)-1-phenylethanolresponse surface methodologyasymmetric bioreductionacetone powderenantioselectivity
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Atak Gunay Baydar Bayraktar Emine Mehmetoglu Ülkü
spellingShingle	Atak Gunay Baydar Bayraktar Emine Mehmetoglu Ülkü Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst Green Processing and Synthesis (s)-1-phenylethanol response surface methodology asymmetric bioreduction acetone powder enantioselectivity
author_facet	Atak Gunay Baydar Bayraktar Emine Mehmetoglu Ülkü
author_sort	Atak Gunay Baydar
title	Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
title_short	Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
title_full	Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
title_fullStr	Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
title_full_unstemmed	Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst
title_sort	optimization of the asymmetric synthesis of (s)-1-phenylethanol using ispir bean as whole-cell biocatalyst
publisher	De Gruyter
series	Green Processing and Synthesis
issn	2191-9550
publishDate	2019-01-01
description	In this study, enantiomerically pure (S)-1-phenylethanol was produced via asymmetric bioreduction of acetophenone. Ispir bean (Phaseolus vulgaris) was used as an alcohol dehydrogenase (ADH) source since whole cells are cheaper than isolated enzymes. Acetone powder methodology was applied for biocatalyst. Glucose was used as a cosubstrate in-order to regenerate cofactor (NADPH). The reactions were carried out in an orbital shaker whose temperature and agitation rate can be controlled. (S)-1-phenylethanol concentration was analyzed by HPLC using a Chiralcel OB column. Effects of the reaction time, substrate concentration, cosubstrate concentration and biocatalyst concentration on the (S)-1-phenylethanol production were investigated using Response Surface Methodology (RSM). 36 h bioreduction time, 6 mM acetophenone concentration, 25.15 mM glucose concentration, and 175 mg/mL biocatalyst concentration were determined as optimum values. In these conditions, 2.4 mM (S)-1-phenylethanol was obtained in phosphate buffer (pH=7.0) at 30°C with >99% enantiomeric excess.
topic	(s)-1-phenylethanol response surface methodology asymmetric bioreduction acetone powder enantioselectivity
url	https://doi.org/10.1515/gps-2019-0021
work_keys_str_mv	AT atakgunaybaydar optimizationoftheasymmetricsynthesisofs1phenylethanolusingispirbeanaswholecellbiocatalyst AT bayraktaremine optimizationoftheasymmetricsynthesisofs1phenylethanolusingispirbeanaswholecellbiocatalyst AT mehmetogluulku optimizationoftheasymmetricsynthesisofs1phenylethanolusingispirbeanaswholecellbiocatalyst
_version_	1716848105964437504

Optimization of the asymmetric synthesis of (S)-1-phenylethanol using Ispir bean as whole-cell biocatalyst

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