Article (Scientific journals)
Use of lipases for the kinetic resolution of lactic acid esters in heptane or in a solvent free system
Richard, Gaetan; Nott, Katherine; Nicks, François et al.
2013In Journal of Molecular Catalysis B: Enzymatic, 97, p. 289-296
Peer Reviewed verified by ORBi
 

Files


Full Text
Use of lipases for the kinetic resolution.pdf
Publisher postprint (1.46 MB)
Request a copy

All documents in ORBi are protected by a user license.

Send to



Details



Keywords :
Candida antarctica lipase B; Enantioselective acylation; Enzyme catalysis; Lactate esters; Secondary alcohols
Abstract :
[en] tKinetic resolution of d,l-ethyl lactate (d,l-LA-Et) and d,l-butyl lactate (d,l-LA-Bu) was accomplished inthe presence of lipases. Transesterification of the lactate esters with alcohols was shown to be poorlyenantioselective, with a very low preference toward the l enantiomer. However, esterification of the freehydroxyl function of the lactate esters was much more enantioselective, with an opposite preferencetoward the d form. Among the 200 combinations screened (substrates and lipases), only two reactionsfulfilled the required criteria for an efficient resolution (fast reaction, enantioselectivity ratio higherthan 100). The best resolution was obtained by esterification of d,l-LA-Bu with butyric anhydride inthe presence of lipase B from Candida antarctica (CAL-B) in heptane (at 30◦C): LA-Bu was resolved in6 h with an initial esterification rate of d-LA-BU of 1.5 g L−1h−1g−1EZ, an enantioselectivity ratio higherthan 100, a l substrate consumption lower than 1%, and a final substrate enantiomeric excess superiorto 99%. After having demonstrated that neither LA-Bu nor BuAn were inhibitors of CAL-B, the reactionwas further improved by carrying it out in a solvent free system, at an elevated temperature (60◦C), andat a higher lipase concentration. LA-Bu was resolved in 6 h with an initial rate of 7.6 g L−1h−1g−1EZ, anenantioselectivity ratio higher than 100, and a final substrate enantiomeric excess of 95%.
Disciplines :
Food science
Author, co-author :
Richard, Gaetan ;  Université de Liège - ULiège > Chimie et bio-industries > Analyse, qual. et risques - Labo. de Chimie analytique
Nott, Katherine ;  Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Nicks, François
Paquot, Michel ;  Université de Liège - ULiège > Chimie et bio-industries > Chimie biologique industrielle
Blecker, Christophe ;  Université de Liège - ULiège > Chimie et bio-industries > Science des alim. et formul.
Fauconnier, Marie-Laure  ;  Université de Liège - ULiège > Chimie et bio-industries > Chimie générale et organique
Language :
English
Title :
Use of lipases for the kinetic resolution of lactic acid esters in heptane or in a solvent free system
Publication date :
05 September 2013
Journal title :
Journal of Molecular Catalysis B: Enzymatic
ISSN :
1381-1177
eISSN :
1873-3158
Publisher :
Elsevier Science, Amsterdam, Netherlands
Volume :
97
Pages :
289-296
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 15 October 2013

Statistics


Number of views
148 (29 by ULiège)
Number of downloads
94 (12 by ULiège)

Scopus citations®
 
2
Scopus citations®
without self-citations
2
OpenCitations
 
2

Bibliography


Similar publications



Contact ORBi