Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes
The lipase-catalyzed synthesis of thiamphenicol derivatives has been studied through complementary acylation and hydrolytic approaches, finding Candida antarctica lipase B as the most efficient biocatalyst for the selective modification of both thiamphenicol and thiamphenicol diacetate, respectively...
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Sociedade Brasileira de Química
2014
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ftjscielo:oai:scielo:S0103-50532014000600001 2023-05-15T13:44:23+02:00 Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes Silva,Marcos R. da Montenegro,Tasso G. C. Mattos,Marcos C. de Oliveira,Maria da Conceição F. de Lemos,Telma L. G. de Gonzalo,Gonzalo de Lavandera,Iván Gotor-Fernández,Vicente Gotor,Vicente 2014-06-01 text/html http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000600001 en eng Sociedade Brasileira de Química Journal of the Brazilian Chemical Society v.25 n.6 2014 biocatalysis lipases medium engineering regioselective processes thiamphenicol journal article 2014 ftjscielo 2015-10-26T20:48:38Z The lipase-catalyzed synthesis of thiamphenicol derivatives has been studied through complementary acylation and hydrolytic approaches, finding Candida antarctica lipase B as the most efficient biocatalyst for the selective modification of both thiamphenicol and thiamphenicol diacetate, respectively. The best results have been obtained using acylation reactions with different vinyl esters of variable length, yielding the corresponding 3'-monoesters with excellent yields and in short reaction times. The conditions have been analyzed in terms of substrate concentration, enzyme loading and type of acyl donor. The reuse of the enzyme for five-times without significant loss of the activity has also been demonstrated. Alternatively, the hydrolytic approach has allowed the preparation of some 1'-monoesters in good yields, although the reactivity and selectivity levels were lower than the ones achieved for the complementary acetylation reaction. Article in Journal/Newspaper Antarc* Antarctica SciELO Brazil (Scientific Electronic Library Online) |
institution |
Open Polar |
collection |
SciELO Brazil (Scientific Electronic Library Online) |
op_collection_id |
ftjscielo |
language |
English |
topic |
biocatalysis lipases medium engineering regioselective processes thiamphenicol |
spellingShingle |
biocatalysis lipases medium engineering regioselective processes thiamphenicol Silva,Marcos R. da Montenegro,Tasso G. C. Mattos,Marcos C. de Oliveira,Maria da Conceição F. de Lemos,Telma L. G. de Gonzalo,Gonzalo de Lavandera,Iván Gotor-Fernández,Vicente Gotor,Vicente Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
topic_facet |
biocatalysis lipases medium engineering regioselective processes thiamphenicol |
description |
The lipase-catalyzed synthesis of thiamphenicol derivatives has been studied through complementary acylation and hydrolytic approaches, finding Candida antarctica lipase B as the most efficient biocatalyst for the selective modification of both thiamphenicol and thiamphenicol diacetate, respectively. The best results have been obtained using acylation reactions with different vinyl esters of variable length, yielding the corresponding 3'-monoesters with excellent yields and in short reaction times. The conditions have been analyzed in terms of substrate concentration, enzyme loading and type of acyl donor. The reuse of the enzyme for five-times without significant loss of the activity has also been demonstrated. Alternatively, the hydrolytic approach has allowed the preparation of some 1'-monoesters in good yields, although the reactivity and selectivity levels were lower than the ones achieved for the complementary acetylation reaction. |
format |
Article in Journal/Newspaper |
author |
Silva,Marcos R. da Montenegro,Tasso G. C. Mattos,Marcos C. de Oliveira,Maria da Conceição F. de Lemos,Telma L. G. de Gonzalo,Gonzalo de Lavandera,Iván Gotor-Fernández,Vicente Gotor,Vicente |
author_facet |
Silva,Marcos R. da Montenegro,Tasso G. C. Mattos,Marcos C. de Oliveira,Maria da Conceição F. de Lemos,Telma L. G. de Gonzalo,Gonzalo de Lavandera,Iván Gotor-Fernández,Vicente Gotor,Vicente |
author_sort |
Silva,Marcos R. da |
title |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
title_short |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
title_full |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
title_fullStr |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
title_full_unstemmed |
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
title_sort |
regioselective preparation of thiamphenicol esters through lipase-catalyzed processes |
publisher |
Sociedade Brasileira de Química |
publishDate |
2014 |
url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000600001 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
Journal of the Brazilian Chemical Society v.25 n.6 2014 |
_version_ |
1766201130245685248 |