Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts

doi:10.1007/s13659-016-0118-2

应用天然产物 ›› 2017, Vol. 7 ›› Issue (1): 171-179.DOI: 10.1007/s13659-016-0118-2

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Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts

Swetha Ettireddy, Vijitha Chandupatla, Ciddi Veeresham

University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana 506 009, India

收稿日期:2016-07-29 修回日期:2016-12-30 出版日期:2017-02-24 发布日期:2018-02-06
通讯作者: Ciddi Veeresham,e-mail:ciddiveeresham@yahoo.co.in
基金资助:
Authors are thankful for the financial assistance (SR/SO/HS/0087/2010) given by Science and Engineering Research Board, DST, New Delhi, India. Authors are also thankful to Symed labs Ltd., Medak, India, for the kind gift of racemic Carvedilol.

Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts

Swetha Ettireddy, Vijitha Chandupatla, Ciddi Veeresham

University College of Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana 506 009, India

Received:2016-07-29 Revised:2016-12-30 Online:2017-02-24 Published:2018-02-06
About author:10.1007/s13659-016-0118-2
Supported by:
Authors are thankful for the financial assistance (SR/SO/HS/0087/2010) given by Science and Engineering Research Board, DST, New Delhi, India. Authors are also thankful to Symed labs Ltd., Medak, India, for the kind gift of racemic Carvedilol.

摘要/Abstract

摘要： Among the microorganisms employed in the study, Aspergillus niger (GUFCC5443), Escherichia coli (ATCC9637), Streptomyces halstedii (CKM-2), Pseudomonas putida (NCIB9494), Cunninghamella elegans (NCIM689) and Sphingomonas paucimobilis (NCTC11030) were capable for the enantioselective conversion of racemic Carvedilol. Immobilization technique enhanced the enantioselectivity of microorganisms and thus increased the enantiomeric purity of the drug. Excellent enantiomeric ratios (E) were found in reactions catalyzed by immobilized A. niger and E. coli with values 174.44 and 104.26, respectively. Triacylglycerol lipase from Aspergillus niger was also employed in this study as a biocatalyst which resulted in the product with 83.35% enantiomeric excess (ee) and E of 11.34 while the enzyme on immobilization has yielded 99.08% ee and 216.39 E. The conversion yield (C%) of the drug by free-enzyme was 57.42%, which was enhanced by immobilization to 90.51%. Hence, our results suggest that immobilized triacylglycerol lipase from A. niger (Lipase AP6) could be an efficient biocatalyst for the enantioselective resolution of racemic Carvedilol to (S)-(-)- Carvedilol with high enantiomeric purity followed by immobilized cultures of A. niger and E. coli.

关键词: Carvedilol, Whole-cell microorganisms, Triacylglycerol lipase, Immobilization, Stereoinversion

Abstract: Among the microorganisms employed in the study, Aspergillus niger (GUFCC5443), Escherichia coli (ATCC9637), Streptomyces halstedii (CKM-2), Pseudomonas putida (NCIB9494), Cunninghamella elegans (NCIM689) and Sphingomonas paucimobilis (NCTC11030) were capable for the enantioselective conversion of racemic Carvedilol. Immobilization technique enhanced the enantioselectivity of microorganisms and thus increased the enantiomeric purity of the drug. Excellent enantiomeric ratios (E) were found in reactions catalyzed by immobilized A. niger and E. coli with values 174.44 and 104.26, respectively. Triacylglycerol lipase from Aspergillus niger was also employed in this study as a biocatalyst which resulted in the product with 83.35% enantiomeric excess (ee) and E of 11.34 while the enzyme on immobilization has yielded 99.08% ee and 216.39 E. The conversion yield (C%) of the drug by free-enzyme was 57.42%, which was enhanced by immobilization to 90.51%. Hence, our results suggest that immobilized triacylglycerol lipase from A. niger (Lipase AP6) could be an efficient biocatalyst for the enantioselective resolution of racemic Carvedilol to (S)-(-)- Carvedilol with high enantiomeric purity followed by immobilized cultures of A. niger and E. coli.

Key words: Carvedilol, Whole-cell microorganisms, Triacylglycerol lipase, Immobilization, Stereoinversion

Swetha Ettireddy, Vijitha Chandupatla, Ciddi Veeresham. Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts[J]. 应用天然产物, 2017, 7(1): 171-179.

Swetha Ettireddy, Vijitha Chandupatla, Ciddi Veeresham. Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts[J]. Natural Products and Bioprospecting, 2017, 7(1): 171-179.

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Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts

Enantioselective Resolution of (R, S)-Carvedilol to (S)-(-)-Carvedilol by Biocatalysts

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