Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis

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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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Detalles Bibliográficos
Autor principal: Rozenberg, G.I
Otros Autores: Espada, J., De Cidre, L.L, Eiján, A.M, Calvo, J.C, Bertolesi, G.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2001
Acceso en línea:Registro en Scopus
DOI
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Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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024 7 |2 scopus  |a 2-s2.0-0035175643 
024 7 |2 pubmed  |a 11197157 
024 7 |2 cas  |a 2-norbornene, 498-66-8; beta-Cyclodextrins; betadex, 7585-39-9; Cyclodextrins; Ethers; Norbornanes 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a ELCTD 
100 1 |a Rozenberg, G.I. 
245 1 0 |a Evaluation of norbornene-β-cyclodextrin-based monomers and oligomers as chiral selectors by means of nonaqueous capillary electrophoresis 
260 |c 2001 
270 1 0 |m Huber, C.G.; Inst. of Analyt. Chem./Radiochem., University of Innsbruck, Innrain 52a, A-6020 Innsbruck, Austria; email: christian.huber@uibk.ac.at 
506 |2 openaire  |e Política editorial 
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504 |a Fanali, S., (2000) J. Chromatogr. A, 875, pp. 89-122 
504 |a Wang, F., Khaledi, M.G., (2000) J. Chromatogr. A, 875, pp. 277-293 
504 |a Valkó, I.E., Sirén, H., Riekkola, M.-L., (1996) Chromatographia, 43, pp. 242-246 
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504 |a Schwab, P., Grubbs, R.H., Ziller, J.W., (1996) J. Am. Chem. Soc., 118, pp. 100-110 
504 |a Khan, A.R., Forgo, P., Stine, K.J., D'Souza, V.T., (1998) Chem. Rev., 98, pp. 1977-1996 
504 |a Valkó, I.E., Sirén, H., Riekkola, M.-L., (1996) J. Chromatogr. A, 737, pp. 263-272 
504 |a Ward, T.J., Dann III, C., Blaylock, A., (1995) J. Chromatogr. A, 715, pp. 337-344 
504 |a Baker, D.R., (1995) Capillary Electrophoresis, pp. 94-158. , Wiley New York 
504 |a Tjørnelund, J., Hansen, S.H., (1997) Chromatographia, 44, pp. 5-9 
520 3 |a 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).  |l eng 
593 |a Departamento de Química Biolgica, Madrid, Argentina 
593 |a Departamento de Ciencas Biolgicas, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina 
593 |a Instituto de Investigaciones Biomédicas, Consejo Superior de Investigaciones Científicas, Universidad Autnoma de Madrid, Madrid, Spain 
593 |a Instituto de Oncología A.H.Roffo, Universidad de Buenos Aires, Argentina 
593 |a Departamento de Química Biolgica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina 
690 1 0 |a DANSYL AMINO ACIDS 
690 1 0 |a MONOMERIC AND OLIGOMERIC Β-CYCLODEXTRINS 
690 1 0 |a NONAQUEOUS CAPILLARY ELECTROPHORESIS 
690 1 0 |a AMINO ACID DERIVATIVE 
690 1 0 |a BETA CYCLODEXTRIN DERIVATIVE 
690 1 0 |a BICARBONATE 
690 1 0 |a CARBOXYLIC ACID DERIVATIVE 
690 1 0 |a DANSYL CHLORIDE 
690 1 0 |a ELECTROLYTE 
690 1 0 |a ESTER 
690 1 0 |a MONOMER 
690 1 0 |a N METHYLFORMAMIDE 
690 1 0 |a NORBORNENE DERIVATIVE 
690 1 0 |a OLIGOMER 
690 1 0 |a SILANE DERIVATIVE 
690 1 0 |a AQUEOUS SOLUTION 
690 1 0 |a ARTICLE 
690 1 0 |a CAPILLARY ELECTROPHORESIS 
690 1 0 |a CHIRALITY 
690 1 0 |a ENANTIOMER 
690 1 0 |a OPTICAL RESOLUTION 
690 1 0 |a POLYMERIZATION 
690 1 0 |a BETA-CYCLODEXTRINS 
690 1 0 |a CARBOHYDRATE SEQUENCE 
690 1 0 |a CYCLODEXTRINS 
690 1 0 |a ELECTROPHORESIS, CAPILLARY 
690 1 0 |a ETHERS 
690 1 0 |a MOLECULAR SEQUENCE DATA 
690 1 0 |a MOLECULAR STRUCTURE 
690 1 0 |a NORBORNANES 
700 1 |a Espada, J. 
700 1 |a De Cidre, L.L. 
700 1 |a Eiján, A.M. 
700 1 |a Calvo, J.C. 
700 1 |a Bertolesi, G.E. 
773 0 |d 2001  |g v. 22  |h pp. 109-116  |k n. 1  |p Electrophoresis  |x 01730835  |w (AR-BaUEN)CENRE-4560  |t Electrophoresis 
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856 4 0 |u https://doi.org/10.1002/1522-2683(200101)22:1<109::AID-ELPS109>3.0.CO;2-P  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_01730835_v22_n1_p109_Rozenberg  |y Handle 
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999 |c 63053 

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