Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen

The purpose of this research was to study the effect of the methyl branching of a high log P alkane solvent and the water activity in the organic medium on the initial rate and the enantioselectivity of ibuprofen esterification catalyzed by Candida rugosa lipase. Resolution of ibuprofen is important...

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Autores principales:	Gottemukkala,Vijay V, Saripella,Kalyan K, Kadari,Anil K, Neau,Steven H
Lenguaje:	English
Publicado:	Pontificia Universidad Católica de Valparaíso 2008
Materias:	enantioselective esterification ibuprofen lipase solvent-effect water activity
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582008000100002
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spelling	oai:scielo:S0717-345820080001000022008-10-28Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofenGottemukkala,Vijay VSaripella,Kalyan KKadari,Anil KNeau,Steven H enantioselective esterification ibuprofen lipase solvent-effect water activity The purpose of this research was to study the effect of the methyl branching of a high log P alkane solvent and the water activity in the organic medium on the initial rate and the enantioselectivity of ibuprofen esterification catalyzed by Candida rugosa lipase. Resolution of ibuprofen is important because S-(+)-ibuprofen has the desired pharmacological activity, whereas the R-(-)-enantiomer causes much of the side effects. The Candida rugosa lipase-catalyzed reaction in isooctane at 40ºC and 0.73 water activity gave the best results, both in terms of the initial reaction rate and the enantioselectivity of the reaction. An increase in water activity allowed a higher reaction rate and enantiomeric excess in each of the four solvents. An increase in methyl branching did not necessarily increase the initial reaction rate, but it allowed a higher enantioselectivity, evidenced by an increase in the substrate enantiomeric excessinfo:eu-repo/semantics/openAccessPontificia Universidad Católica de ValparaísoElectronic Journal of Biotechnology v.11 n.1 20082008-01-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582008000100002en10.4067/S0717-34582008000100002
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	enantioselective esterification ibuprofen lipase solvent-effect water activity
spellingShingle	enantioselective esterification ibuprofen lipase solvent-effect water activity Gottemukkala,Vijay V Saripella,Kalyan K Kadari,Anil K Neau,Steven H Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
description	The purpose of this research was to study the effect of the methyl branching of a high log P alkane solvent and the water activity in the organic medium on the initial rate and the enantioselectivity of ibuprofen esterification catalyzed by Candida rugosa lipase. Resolution of ibuprofen is important because S-(+)-ibuprofen has the desired pharmacological activity, whereas the R-(-)-enantiomer causes much of the side effects. The Candida rugosa lipase-catalyzed reaction in isooctane at 40ºC and 0.73 water activity gave the best results, both in terms of the initial reaction rate and the enantioselectivity of the reaction. An increase in water activity allowed a higher reaction rate and enantiomeric excess in each of the four solvents. An increase in methyl branching did not necessarily increase the initial reaction rate, but it allowed a higher enantioselectivity, evidenced by an increase in the substrate enantiomeric excess
author	Gottemukkala,Vijay V Saripella,Kalyan K Kadari,Anil K Neau,Steven H
author_facet	Gottemukkala,Vijay V Saripella,Kalyan K Kadari,Anil K Neau,Steven H
author_sort	Gottemukkala,Vijay V
title	Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
title_short	Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
title_full	Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
title_fullStr	Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
title_full_unstemmed	Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
title_sort	effect of methyl branching of c8h18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen
publisher	Pontificia Universidad Católica de Valparaíso
publishDate	2008
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-34582008000100002
work_keys_str_mv	AT gottemukkalavijayv effectofmethylbranchingofc8h18alkanesandwateractivityonlipasecatalyzedenantioselectiveesterificationofibuprofen AT saripellakalyank effectofmethylbranchingofc8h18alkanesandwateractivityonlipasecatalyzedenantioselectiveesterificationofibuprofen AT kadarianilk effectofmethylbranchingofc8h18alkanesandwateractivityonlipasecatalyzedenantioselectiveesterificationofibuprofen AT neaustevenh effectofmethylbranchingofc8h18alkanesandwateractivityonlipasecatalyzedenantioselectiveesterificationofibuprofen
_version_	1718441777806966784

Effect of methyl branching of C8H18 alkanes and water activity on lipase-catalyzed enantioselective esterification of ibuprofen

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