Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography
Autor(a) principal: | |
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Data de Publicação: | 2007 |
Outros Autores: | , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700012 |
Resumo: | Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain aminoacid racemates. Chiral selector was copper L-phenylalaninate (II) and the results showed the elution of D enantiomer followed by L form. Considering the 3-point interaction concept, a mechanism of chiral recognition was proposed, in which no change of configuration would follow the formation of pseudo-homochiral and heterochiral complexes. To prove the reliability of this mechanism, the trans configuration of homochiral complex had to be more stable than the cis form, which was confirmed by DFT-B3LYP calculation in gas phase. The infrared frequencies were also calculated and the comparison with the subtracted and deconvoluted spectrum of the in-solution complex also pointed to the presence of the trans diasteroisomer. |
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Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatographyalpha-amino acidsL-phenylalanineligand exchange chromatographyab initio molecular orbital calculationsfourier self-deconvolutionLigand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain aminoacid racemates. Chiral selector was copper L-phenylalaninate (II) and the results showed the elution of D enantiomer followed by L form. Considering the 3-point interaction concept, a mechanism of chiral recognition was proposed, in which no change of configuration would follow the formation of pseudo-homochiral and heterochiral complexes. To prove the reliability of this mechanism, the trans configuration of homochiral complex had to be more stable than the cis form, which was confirmed by DFT-B3LYP calculation in gas phase. The infrared frequencies were also calculated and the comparison with the subtracted and deconvoluted spectrum of the in-solution complex also pointed to the presence of the trans diasteroisomer.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700012Journal of the Brazilian Chemical Society v.18 n.7 2007reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532007000700012info:eu-repo/semantics/openAccessSenra,Jaqueline D.Malta,Luiz Fernando B.Ceva-Antunes,Patricia M. N.Corrêa,Rodrigo J.Antunes,O. A. C.eng2008-01-08T00:00:00Zoai:scielo:S0103-50532007000700012Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2008-01-08T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
title |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
spellingShingle |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography Senra,Jaqueline D. alpha-amino acids L-phenylalanine ligand exchange chromatography ab initio molecular orbital calculations fourier self-deconvolution |
title_short |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
title_full |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
title_fullStr |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
title_full_unstemmed |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
title_sort |
Elucidation of chiral Recognition mechanism of alpha-amino acids using ligand exchange high performance liquid chromatography |
author |
Senra,Jaqueline D. |
author_facet |
Senra,Jaqueline D. Malta,Luiz Fernando B. Ceva-Antunes,Patricia M. N. Corrêa,Rodrigo J. Antunes,O. A. C. |
author_role |
author |
author2 |
Malta,Luiz Fernando B. Ceva-Antunes,Patricia M. N. Corrêa,Rodrigo J. Antunes,O. A. C. |
author2_role |
author author author author |
dc.contributor.author.fl_str_mv |
Senra,Jaqueline D. Malta,Luiz Fernando B. Ceva-Antunes,Patricia M. N. Corrêa,Rodrigo J. Antunes,O. A. C. |
dc.subject.por.fl_str_mv |
alpha-amino acids L-phenylalanine ligand exchange chromatography ab initio molecular orbital calculations fourier self-deconvolution |
topic |
alpha-amino acids L-phenylalanine ligand exchange chromatography ab initio molecular orbital calculations fourier self-deconvolution |
description |
Ligand exchange HPLC technique was applied to resolve chiral separation of aliphatic side chain aminoacid racemates. Chiral selector was copper L-phenylalaninate (II) and the results showed the elution of D enantiomer followed by L form. Considering the 3-point interaction concept, a mechanism of chiral recognition was proposed, in which no change of configuration would follow the formation of pseudo-homochiral and heterochiral complexes. To prove the reliability of this mechanism, the trans configuration of homochiral complex had to be more stable than the cis form, which was confirmed by DFT-B3LYP calculation in gas phase. The infrared frequencies were also calculated and the comparison with the subtracted and deconvoluted spectrum of the in-solution complex also pointed to the presence of the trans diasteroisomer. |
publishDate |
2007 |
dc.date.none.fl_str_mv |
2007-01-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700012 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000700012 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532007000700012 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.18 n.7 2007 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318168522358784 |