Literature DB >> 16680456

Optimization of enantioselective resolution of racemic ibuprofen by native lipase from Aspergillus niger.

Patrícia de O Carvalho1, Fabiano J Contesini, Renato Bizaco, Silvana Ap Calafatti, Gabriela A Macedo.   

Abstract

Resolution of (R,S)-ibuprofen (2-(4-isobutylphenyl)propionic acid) enantiomers by esterification reaction with 1-propanol in different organic solvents was studied using native Aspergillus niger lipase. The main variables controlling the process (enzyme concentration and 1-propanol:ibuprofen molar ratio) have been optimized using response surface methodology based on a five-level, two-variable central composite rotatable design, in which the selected objective function was enantioselectivity. This enzyme preparation showed preferentially catalyzes the esterification of R(-)-ibuprofen, and under optimum conditions (7% w/v of enzyme and molar ratio of 2.41:1) the enantiomeric excess of active S(+)-ibuprofen and total conversion values were 79.1 and 48.0%, respectively, and the E-value was 32, after 168 h of reaction in isooctane.

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Year:  2006        PMID: 16680456     DOI: 10.1007/s10295-006-0138-8

Source DB:  PubMed          Journal:  J Ind Microbiol Biotechnol        ISSN: 1367-5435            Impact factor:   3.346


  14 in total

1.  Solvent effect on lipase enantioselectivity. Evidence for the presence of two thermodynamic states.

Authors:  P L Overbeeke; J A Jongejan; J J Heijnen
Journal:  Biotechnol Bioeng       Date:  2000-11-05       Impact factor: 4.530

2.  Lipase-catalyzed enantioselective esterification of (S)-naproxen hydroxyalkyl ester in organic media.

Authors:  Chun-Sheng Chang; Chin-Shuo Hsu; Chun-Sheng Shang
Journal:  Biotechnol Lett       Date:  2003-03       Impact factor: 2.461

3.  Kinetic resolution of ibuprofen catalyzed by Candida rugosa lipase in ionic liquids.

Authors:  Yu Hongwei; Wu Jinchuan; Ching Chi Bun
Journal:  Chirality       Date:  2005-01       Impact factor: 2.437

4.  Purification of extracellular lipase from Pseudomonas aeruginosa.

Authors:  W Stuer; K E Jaeger; U K Winkler
Journal:  J Bacteriol       Date:  1986-12       Impact factor: 3.490

5.  Enzymatic catalysis in nonaqueous solvents.

Authors:  A Zaks; A M Klibanov
Journal:  J Biol Chem       Date:  1988-03-05       Impact factor: 5.157

Review 6.  Enzymes in the synthesis of chiral drugs.

Authors:  A L Margolin
Journal:  Enzyme Microb Technol       Date:  1993-04       Impact factor: 3.493

7.  The importance of stereochemistry in the clinical pharmacokinetics of the 2-arylpropionic acid non-steroidal anti-inflammatory drugs.

Authors:  A J Hutt; J Caldwell
Journal:  Clin Pharmacokinet       Date:  1984 Jul-Aug       Impact factor: 6.447

Review 8.  Bacterial lipases.

Authors:  K E Jaeger; S Ransac; B W Dijkstra; C Colson; M van Heuvel; O Misset
Journal:  FEMS Microbiol Rev       Date:  1994-09       Impact factor: 16.408

9.  Enantioselective esterification of racemic naproxen by lipases in organic solvent.

Authors:  S W Tsai; H J Wei
Journal:  Enzyme Microb Technol       Date:  1994-04       Impact factor: 3.493

10.  Use of lipases in the resolution of racemic ibuprofen.

Authors:  A Mustranta
Journal:  Appl Microbiol Biotechnol       Date:  1992-10       Impact factor: 4.813

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  2 in total

1.  Extremely thermostable esterases from the thermoacidophilic euryarchaeon Picrophilus torridus.

Authors:  Matthias Hess; Moritz Katzer; Garabed Antranikian
Journal:  Extremophiles       Date:  2008-03-11       Impact factor: 2.395

2.  Response surface analysis for the production of an enantioselective lipase from Aspergillus niger by solid-state fermentation.

Authors:  Fabiano Jares Contesini; Vania Castriani Fernades da Silva; Rafael Ferreira Maciel; Rosemary Joana de Lima; Francisco Fábio Cavalcante Barros; Patrícia de Oliveira Carvalho
Journal:  J Microbiol       Date:  2009-10-24       Impact factor: 3.422

  2 in total

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