Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

Paweł Borowiecki , Maria Bretner

Abstract

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.
Author Paweł Borowiecki (FC / IBC / DDTB)
Paweł Borowiecki,,
- Department Of Drug Technology And Biotechnology
, Maria Bretner (FC / IBC / DDTB)
Maria Bretner,,
- Department Of Drug Technology And Biotechnology
Journal seriesTetrahedron-Asymmetry, ISSN 0957-4166
Issue year2013
Vol24
No15-16
Pages925-936
Publication size in sheets0.55
ASJC Classification1604 Inorganic Chemistry; 1605 Organic Chemistry; 1606 Physical and Theoretical Chemistry; 1503 Catalysis
DOIDOI:10.1016/j.tetasy.2013.06.004
URL http://www.sciencedirect.com/science/article/pii/S0957416613002607
Languageen angielski
File
Tetrahedron-Asymmetry.pdf 956.39 KB
Score (nominal)25
Score sourcejournalList
ScoreMinisterial score = 25.0, 02-02-2020, ArticleFromJournal
Ministerial score (2013-2016) = 25.0, 02-02-2020, ArticleFromJournal
Publication indicators Scopus Citations = 14; WoS Citations = 13; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 0.716; WoS Impact Factor: 2013 = 2.165 (2) - 2013=2.097 (5)
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