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CE-MS characterization of negatively charged alpha-, beta- and gamma-CD derivatives and their application to the separation of dipeptide and tripeptide enantiomers by CE.
Electrophoresis. 2010 May; 31(9):1498-505.E

Abstract

Sulfated, sulfopropyl and carboxymethyl alpha-, beta- and gamma-CDs were characterized by CE-ESI-MS using an acidic BGE with anodic MS detection and a basic BGE with cathodic MS detection. Isomers of the sulfated CDs comigrated in both systems. The acidic BGE with anodic MS detection resulted in slightly better separation of the isomers of the sulfopropyl CDs, which were separated according to the number of substituents. In the case of carboxymethyl CDs, isomers with an identical number of substituents but with a different substitution pattern with regard to substitution of the primary and secondary hydroxyl groups of the CDs could be separated using the basic BGE. The separation of the LL and DD enantiomers of dipeptides and tripeptides using the CDs was studied with regard to the amino acid sequence and the nature of the CDs. Standardized conditions with regard to buffer pH, CD concentration and voltage were applied. The peptides were analyzed at pH 2.5 as positively charged compounds and at pH 5.3 as neutral zwitterions. The beta-CD derivatives were more effective chiral selectors for the investigated peptides followed by the alpha-CD derivatives. The gamma-CDs were the least effective selectors. The enantiomer migration order depended on both the CD and the amino acid sequence of the peptides. For several combinations, pH-dependent reversal of the enantiomer migration order was also observed.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Sungthong B
Department of Medicinal/Pharmaceutical Chemistry, School of Pharmacy, University of Jena, Jena, Germany.
Iványi R
No affiliation info available
Bunz SC
No affiliation info available
Neusüss C
No affiliation info available
Scriba GK
No affiliation info available

MeSH

CyclodextrinsDipeptidesElectrophoresis, CapillaryHydrogen-Ion ConcentrationOligopeptidesSpectrometry, Mass, Electrospray IonizationStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20376814

Citation

Sungthong, Bunleu, et al. "CE-MS Characterization of Negatively Charged Alpha-, Beta- and gamma-CD Derivatives and Their Application to the Separation of Dipeptide and Tripeptide Enantiomers By CE." Electrophoresis, vol. 31, no. 9, 2010, pp. 1498-505.
Sungthong B, Iványi R, Bunz SC, et al. CE-MS characterization of negatively charged alpha-, beta- and gamma-CD derivatives and their application to the separation of dipeptide and tripeptide enantiomers by CE. Electrophoresis. 2010;31(9):1498-505.
Sungthong, B., Iványi, R., Bunz, S. C., Neusüss, C., & Scriba, G. K. (2010). CE-MS characterization of negatively charged alpha-, beta- and gamma-CD derivatives and their application to the separation of dipeptide and tripeptide enantiomers by CE. Electrophoresis, 31(9), 1498-505. https://doi.org/10.1002/elps.200900677
Sungthong B, et al. CE-MS Characterization of Negatively Charged Alpha-, Beta- and gamma-CD Derivatives and Their Application to the Separation of Dipeptide and Tripeptide Enantiomers By CE. Electrophoresis. 2010;31(9):1498-505. PubMed PMID: 20376814.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - CE-MS characterization of negatively charged alpha-, beta- and gamma-CD derivatives and their application to the separation of dipeptide and tripeptide enantiomers by CE. AU - Sungthong,Bunleu, AU - Iványi,Róbert, AU - Bunz,Svenja-Catharina, AU - Neusüss,Christian, AU - Scriba,Gerhard K E, PY - 2010/4/9/entrez PY - 2010/4/9/pubmed PY - 2010/8/6/medline SP - 1498 EP - 505 JF - Electrophoresis JO - Electrophoresis VL - 31 IS - 9 N2 - Sulfated, sulfopropyl and carboxymethyl alpha-, beta- and gamma-CDs were characterized by CE-ESI-MS using an acidic BGE with anodic MS detection and a basic BGE with cathodic MS detection. Isomers of the sulfated CDs comigrated in both systems. The acidic BGE with anodic MS detection resulted in slightly better separation of the isomers of the sulfopropyl CDs, which were separated according to the number of substituents. In the case of carboxymethyl CDs, isomers with an identical number of substituents but with a different substitution pattern with regard to substitution of the primary and secondary hydroxyl groups of the CDs could be separated using the basic BGE. The separation of the LL and DD enantiomers of dipeptides and tripeptides using the CDs was studied with regard to the amino acid sequence and the nature of the CDs. Standardized conditions with regard to buffer pH, CD concentration and voltage were applied. The peptides were analyzed at pH 2.5 as positively charged compounds and at pH 5.3 as neutral zwitterions. The beta-CD derivatives were more effective chiral selectors for the investigated peptides followed by the alpha-CD derivatives. The gamma-CDs were the least effective selectors. The enantiomer migration order depended on both the CD and the amino acid sequence of the peptides. For several combinations, pH-dependent reversal of the enantiomer migration order was also observed. SN - 1522-2683 UR - https://www.unboundmedicine.com/medline/citation/20376814/CE_MS_characterization_of_negatively_charged_alpha__beta__and_gamma_CD_derivatives_and_their_application_to_the_separation_of_dipeptide_and_tripeptide_enantiomers_by_CE_ L2 - https://doi.org/10.1002/elps.200900677 DB - PRIME DP - Unbound Medicine ER -

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