Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis
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....
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| Lenguaje: | English |
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_01730835_v22_n1_p109_Rozenberg |
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todo:paper_01730835_v22_n1_p109_Rozenberg2023-10-03T15:07:40Z Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis Rozenberg, G.I. Espada, J. De Cidre, L.L. Eiján, A.M. Calvo, J.C. Bertolesi, G.E. 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 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). Fil:Rozenberg, G.I. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Eiján, A.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Calvo, J.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Bertolesi, G.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR English info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01730835_v22_n1_p109_Rozenberg |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| language |
English |
| orig_language_str_mv |
English |
| topic |
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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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). |
| format |
JOUR |
| author |
Rozenberg, G.I. Espada, J. De Cidre, L.L. Eiján, A.M. Calvo, J.C. Bertolesi, G.E. |
| author_facet |
Rozenberg, G.I. Espada, J. De Cidre, L.L. Eiján, A.M. Calvo, J.C. Bertolesi, G.E. |
| author_sort |
Rozenberg, G.I. |
| title |
Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| title_short |
Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| title_full |
Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| title_fullStr |
Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| title_full_unstemmed |
Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| title_sort |
evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis |
| url |
http://hdl.handle.net/20.500.12110/paper_01730835_v22_n1_p109_Rozenberg |
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