Artículo
Abstract:
Norbornen-5-yl carboxylic acid and norbornen-5-ylmethylsilyl ether-based β-cyclodextrins (β-CDs) containing up to three norbornene ester and up to five norbornene silyl ether units have been prepared from β-CD and norbornen-5-carboxylic chloride and norbornen-5-ylmethyldichlorosilane, respectively. Oligomers (n = 2-4) were prepared therefrom using ring-opening metathesis polymerization (ROMP). Monomeric and oligomeric substituted β-CDs were evaluated as chiral selectors in nonaqueous capillary zone electrophoresis using 35 mM sodium bicarbonate in N-methylformamide (NMF) as background electrolyte. Both monomeric and oligomeric norbornene ester- and norbornene silyl ether-type selectors showed good enantioresolution for dansylated (DNS-) amino acids using concentrations of the chiral selector of up to 4% w/v. A significant improvement in resolution was observed upon the introduction of up to five norbornene silyl ether units into a β-CD molecule, whereas higher degrees of substitution with norbornen-5-yl-carboxyl groups lead to a reduction in enantioresolution of DNS-amino acids. Thus, pentakis(norbornen-5-ylmethylhydroxysiloxyl)-β-CD turned out to be superior to mono(norbornen-5-ylmethylhydroxysiloxyl)-β-CD in terms of enantioresolution. Moreover, norbornene silyl ether-type selectors were found to be more efficient than norbornene ester-type selectors. Finally, oligomeric selectors were found to possess superior or at least comparable enantioselectivity in the separation of DNS-amino acids compared to the parent monomers. A maximum in enantioresolution was obtained with oligo(pentakis(norbornen-5-ylmethylhydroxysiloxyl)β-CD).
Registro:
| Documento: | Artículo |
| Título: | Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| Autor: | Rozenberg, G.I.; Espada, J.; De Cidre, L.L.; Eiján, A.M.; Calvo, J.C.; Bertolesi, G.E. |
| Filiación: | Departamento de Química Biolgica, Madrid, Argentina Departamento de Ciencas Biolgicas, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina Instituto de Investigaciones Biomédicas, Consejo Superior de Investigaciones Científicas, Universidad Autnoma de Madrid, Madrid, Spain Instituto de Oncología A.H.Roffo, Universidad de Buenos Aires, Argentina Departamento de Química Biolgica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina |
| Idioma: | Inglés |
| Palabras clave: | Dansyl amino acids; Monomeric and oligomeric β-cyclodextrins; Nonaqueous capillary electrophoresis; amino acid derivative; beta cyclodextrin derivative; bicarbonate; carboxylic acid derivative; dansyl chloride; electrolyte; ester; monomer; n methylformamide; norbornene derivative; oligomer; silane derivative; aqueous solution; article; capillary electrophoresis; chirality; enantiomer; optical resolution; polymerization; beta-Cyclodextrins; Carbohydrate Sequence; Cyclodextrins; Electrophoresis, Capillary; Ethers; Molecular Sequence Data; Molecular Structure; Norbornanes |
| Año: | 2001 |
| Volumen: | 22 |
| Número: | 1 |
| Página de inicio: | 109 |
| Página de fin: | 116 |
| DOI: | http://dx.doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P |
| Título revista: | Electrophoresis |
| Título revista abreviado: | Electrophoresis |
| ISSN: | 01730835 |
| CODEN: | ELCTD |
| CAS: | 2-norbornene, 498-66-8; beta-Cyclodextrins; betadex, 7585-39-9; Cyclodextrins; Ethers; Norbornanes |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01730835_v22_n1_p109_Rozenberg |
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Citas:
---------- APA ----------
Rozenberg, G.I., Espada, J., De Cidre, L.L., Eiján, A.M., Calvo, J.C. & Bertolesi, G.E. (2001) . Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis. Electrophoresis, 22(1), 109-116.http://dx.doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P
---------- CHICAGO ----------
Rozenberg, G.I., Espada, J., De Cidre, L.L., Eiján, A.M., Calvo, J.C., Bertolesi, G.E. "Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis" . Electrophoresis 22, no. 1 (2001) : 109-116.http://dx.doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P
---------- MLA ----------
Rozenberg, G.I., Espada, J., De Cidre, L.L., Eiján, A.M., Calvo, J.C., Bertolesi, G.E. "Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis" . Electrophoresis, vol. 22, no. 1, 2001, pp. 109-116.http://dx.doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P
---------- VANCOUVER ----------
Rozenberg, G.I., Espada, J., De Cidre, L.L., Eiján, A.M., Calvo, J.C., Bertolesi, G.E. Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis. Electrophoresis. 2001;22(1):109-116.http://dx.doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P
