Literature DB >> 19212787

Kinetic resolution of alpha-lipoic acid via enzymatic differentiation of a remote stereocenter.

Hong-de Yan1, Zhao Wang, Ling-jie Chen.   

Abstract

Kinetic resolution of alpha-lipoic acid, a case of remote stereocenter discrimination, was accomplished using lipase from Aspergillus oryzae WZ007. Performance of this lipase was investigated for enantioselective esterification of (S)-alpha-lipoic acid, leaving the target product (R)-alpha-lipoic acid in unreacted form. The effects of chain length of alcohol, type of solvent, molar ratio of alcohol:acid, and reaction temperature were studied. The optimum reaction conditions were found to be esterification with n-octanol at 50 degrees C in heptane with an alcohol:acid molar ratio of 5:1. The conversion rate of alpha-lipoic acid was 75.2%, with an enantiomeric excess of 92.5% towards unreacted substrate in a reaction time of 48 h.

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Year:  2009        PMID： 19212787     DOI： 10.1007/s10295-009-0531-1

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


  16 in total

1.  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

2.  Efficient chemoenzymatic synthesis of pelitrexol via enzymic differentiation of a remote stereocenter.

Authors:  Shanghui Hu; Sean Kelly; Steve Lee; Junhua Tao; Erik Flahive
Journal:  Org Lett       Date:  2006-04-13       Impact factor: 6.005

3.  Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase.

Authors:  L J REED; B G DeBUSK; I C GUNSALUS; C S HORNBERGER
Journal:  Science       Date:  1951-07-27       Impact factor: 47.728

4.  Alpha-lipoic acid is an effective inhibitor of human immuno-deficiency virus (HIV-1) replication.

Authors:  A Baur; T Harrer; M Peukert; G Jahn; J R Kalden; B Fleckenstein
Journal:  Klin Wochenschr       Date:  1991-10-02

5.  A structural basis for enantioselective inhibition of Candida rugosa lipase by long-chain aliphatic alcohols.

Authors:  M Holmquist; F Haeffner; T Norin; K Hult
Journal:  Protein Sci       Date:  1996-01       Impact factor: 6.725

6.  Enzymatic catalysis in nonaqueous solvents.

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

7.  The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step.

Authors:  B Adger; M T Bes; G Grogan; R McCague; S Pedragosa-Moreau; S M Roberts; R Villa; P W Wan; A J Willetts
Journal:  Bioorg Med Chem       Date:  1997-02       Impact factor: 3.641

8.  Interplay between lipoic acid and glutathione in the protection against microsomal lipid peroxidation.

Authors:  A Bast; G R Haenen
Journal:  Biochim Biophys Acta       Date:  1988-12-16

9.  Protection from hepatic ischemia/reperfusion injury and improvement of liver regeneration by alpha-lipoic acid.

Authors:  Friedrich Duenschede; Kirsten Erbes; Achim Kircher; Stefanie Westermann; Arno Schad; Nina Riegler; Patrick Ewald; Philipp Dutkowski; Alexandra K Kiemer; Oliver Kempski; Theodor Junginger
Journal:  Shock       Date:  2007-06       Impact factor: 3.454

10.  Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.

Authors:  Marco Angoli; Alessio Barilli; Giordano Lesma; Daniele Passarella; Sergio Riva; Alessandra Silvani; Bruno Danieli
Journal:  J Org Chem       Date:  2003-11-28       Impact factor: 4.354
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  2 in total

1.  Surfactant-modified Aspergillus oryzae lipase as a highly active and enantioselective catalyst for the kinetic resolution of (RS)-1-phenylethanol.

Authors:  Hong De Yan; Bing Han Guo; Zhao Wang; Jun Qing Qian
Journal:  3 Biotech       Date:  2019-06-12       Impact factor: 2.406

Review 2.  Enzymatic synthesis of bioactive compounds with high potential for cosmeceutical application.

Authors:  Io Antonopoulou; Simona Varriale; Evangelos Topakas; Ulrika Rova; Paul Christakopoulos; Vincenza Faraco
Journal:  Appl Microbiol Biotechnol       Date:  2016-06-08       Impact factor: 4.813
  2 in total

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