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Enantiomeric separation of chiral peptide nucleic acid monomers by capillary electrophoresis with charged cyclodextrins.
Electrophoresis. 2003 Aug; 24(15):2698-703.E

Abstract

Direct chiral separation of chiral peptide nucleic acid (PNA) monomers has been achieved for the first time by capillary electrophoresis (CE) with charged cyclodextrins as chiral selectors added to the electrophoretic buffer. Selectively modified 6-deoxy-6-N-histamino-beta-cyclodextrin and sulfobutyl ether-beta-CD were successfully used as chiral selectors for the enantiomeric separation of chiral monomers based on different aminoethylamino acids bearing thymine or adenine as nucleobases. Chiral separations were obtained at low selector concentrations (1-3 mM) with good enantioselectivity and resolution factors. Separations were optimized as a function of pH in order to exploit the effect of the electrostatic interactions between the oppositely charged selector and selectand. The method has been applied to the analysis of the enantiomeric excess of chiral monomers used for the solid phase synthesis of chiral PNA oligomers. CE chiral analysis showed that a very high enantiomeric purity was generally achieved in the synthesis of all monomers, except for histidine and aspartic acid based monomers in which ca. 10% of the "wrong" enantiomer was always present.

Authors+Show Affiliations

Galaverna G
Dipartimento di Chimica Organica e Industriale, Università di Parma, Parco Area della Scienze 17/A, I-43100 Parma, Italy.
Sforza S
No affiliation info available
Tedeschi T
No affiliation info available
Corradini R
No affiliation info available
Dossena A
No affiliation info available
Marchelli R
No affiliation info available

MeSH

CyclodextrinsElectrophoresis, CapillaryHydrogen-Ion ConcentrationPeptide Nucleic AcidsStatic ElectricityStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

12900885

Citation

Galaverna, Gianni, et al. "Enantiomeric Separation of Chiral Peptide Nucleic Acid Monomers By Capillary Electrophoresis With Charged Cyclodextrins." Electrophoresis, vol. 24, no. 15, 2003, pp. 2698-703.
Galaverna G, Sforza S, Tedeschi T, et al. Enantiomeric separation of chiral peptide nucleic acid monomers by capillary electrophoresis with charged cyclodextrins. Electrophoresis. 2003;24(15):2698-703.
Galaverna, G., Sforza, S., Tedeschi, T., Corradini, R., Dossena, A., & Marchelli, R. (2003). Enantiomeric separation of chiral peptide nucleic acid monomers by capillary electrophoresis with charged cyclodextrins. Electrophoresis, 24(15), 2698-703.
Galaverna G, et al. Enantiomeric Separation of Chiral Peptide Nucleic Acid Monomers By Capillary Electrophoresis With Charged Cyclodextrins. Electrophoresis. 2003;24(15):2698-703. PubMed PMID: 12900885.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantiomeric separation of chiral peptide nucleic acid monomers by capillary electrophoresis with charged cyclodextrins. AU - Galaverna,Gianni, AU - Sforza,Stefano, AU - Tedeschi,Tullia, AU - Corradini,Roberto, AU - Dossena,Arnaldo, AU - Marchelli,Rosangela, PY - 2003/8/6/pubmed PY - 2004/6/18/medline PY - 2003/8/6/entrez SP - 2698 EP - 703 JF - Electrophoresis JO - Electrophoresis VL - 24 IS - 15 N2 - Direct chiral separation of chiral peptide nucleic acid (PNA) monomers has been achieved for the first time by capillary electrophoresis (CE) with charged cyclodextrins as chiral selectors added to the electrophoretic buffer. Selectively modified 6-deoxy-6-N-histamino-beta-cyclodextrin and sulfobutyl ether-beta-CD were successfully used as chiral selectors for the enantiomeric separation of chiral monomers based on different aminoethylamino acids bearing thymine or adenine as nucleobases. Chiral separations were obtained at low selector concentrations (1-3 mM) with good enantioselectivity and resolution factors. Separations were optimized as a function of pH in order to exploit the effect of the electrostatic interactions between the oppositely charged selector and selectand. The method has been applied to the analysis of the enantiomeric excess of chiral monomers used for the solid phase synthesis of chiral PNA oligomers. CE chiral analysis showed that a very high enantiomeric purity was generally achieved in the synthesis of all monomers, except for histidine and aspartic acid based monomers in which ca. 10% of the "wrong" enantiomer was always present. SN - 0173-0835 UR - https://www.unboundmedicine.com/medline/citation/12900885/Enantiomeric_separation_of_chiral_peptide_nucleic_acid_monomers_by_capillary_electrophoresis_with_charged_cyclodextrins_ DB - PRIME DP - Unbound Medicine ER -