Studies on the chiral recognition of peptide enantiomers by neutral and sulfated β-cyclodextrin and heptakis-(2,3-di-O-acetyl)-β-cyclodextrin using capillary electrophoresis and nuclear magnetic resonance

Süß, Falko; Kahle, Claudia; Holzgrabe, Ulrike; Scriba, Gerhard K. E.

doi:10.1002/1522-2683(200205)23:9<1301::aid-elps1301>3.0.co;2-7

Cited by 45 publications

(14 citation statements)

References 27 publications

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“…Scriba et al. carried out remarkable work on the chiral separation of di‐ and tripeptide stereoisomers using CDs as chiral selectors . All peptides resolved were unprotected at both termini.…”

Section: Chiral Separation Of Small Peptidesmentioning

confidence: 99%

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Ali

ALOthman

Al–Warthan

et al. 2014

J of Separation Science

133

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Many chemical and biological processes are controlled by the stereochemistry of small polypeptides (di-, tri-, tetra-, penta-, hexapeptides, etc). The biological importance of peptide stereoisomers is of great value. Therefore, the chiral resolution of peptides is an important issue in biological and medicinal sciences and drug industries. The chiral resolutions of peptide racemates have been discussed with the use of capillary electrophoresis and chromatographic techniques. The various chiral selectors used were polysaccharides, cyclodextrins, Pirkle types, macrocyclic antibiotics, crown ethers, imprinted polymers, etc. The stereochemistry of dipeptides is also discussed. Besides, efforts are made to explain the chiral recognition mechanisms, which will be helpful in understanding existing and developing new stereoselective analyses. Future perspectives of enantiomeric resolution are also predicted. Finally, the review concludes with the demand of enantiomeric resolution of all naturally occurring and synthetic peptides.

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Section: Chiral Separation Of Small Peptidesmentioning

confidence: 99%

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Ali

ALOthman

Al–Warthan

et al. 2014

J of Separation Science

133

View full text Add to dashboard Cite

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“…Together with the methyl groups the effect of acetyl substituents located in positions 2 and 3 of b-CD has been studied on the enantiomer affinity pattern of some chiral analytes ( [16,20,21]; Chankvetadze et al, submitted to Electrophoresis; Chankvetadze et al, in preparation).…”

Section: Reversal Of the Enantiomer Affinity Pattern Depending On Thementioning

confidence: 99%

“…One relatively old example of this kind of reversal of the EMO remained confusing for several years [47]. The sound explanation of this observation became possible after the studies by Rizzi and Kremser [9][10][11] and Scriba's group [3,5,6,[13][14][15][16][17].…”

Section: Emo Determined By the Mobility Of Noncovalent Diastereomericmentioning

confidence: 99%

“…Scriba and co-workers have thoroughly studied the enantiomer migration order of small di-and tripeptides in the presence of various neutral [5,6,[13][14][15][16] and charged [13,16,17] CDs. The reversal of the EMO has been observed due to opposite affinity of the small peptide enantiomers towards differently substituted CDs [5,6,[13][14][15][16][17] as well as due to the pH-dependent affinity reversal of the enantiomer towards the same CD [5]. One of the most interesting results of these studies seems to be the reversal of EMO of di-and tripeptides in relatively narrow pH-range 2.5-3.5 [14,15].…”

Section: Emo Determined By the Mobility Of Noncovalent Diastereomericmentioning

confidence: 99%

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Enantiomer migration order in chiral capillary electrophoresis

2002

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Enantiomer migration order (EMO) in chiral capillary electrophoresis (CE) represents a challenging issue, referred to in less than 20% of the articles on CE enantioseparations. This review article will (i) illustrate the actuality of the topic, (ii) discuss some technical problems related to EMO in CE enantioseparations, (iii) examine the principal differences between CE and other separation techniques from the viewpoint of enantiomer elution order, (iv) demonstrate the potential for a designed reversal of EMO in CE, and (v) emphasize the importance of studying EMO for better understanding of chiral CE as well as its more effective application. Along with CE, the results obtained by other instrumental techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), X-ray crystallography, as well as molecular modeling calculations will be shortly discussed. Rather than referring to all published examples of the opposite migration order of enantiomers in CE, the emphasis will be on general aspects. Recently, the reversal of the EMO was described in detail in a book chapter (Chankvetadze, B., Capillary Electrophoresis in Chiral Analysis, Wiley & Sons, Chichester, UK 1997, Chapter 12) as well as in three review articles.

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“…The separation of di-and tripeptides by randomly substituted and single isomer sulfated b-CD derivatives at pH 2.5 has been studied previously [19,20]. As reversal of the enantiomer migration order at pH 5.3 compared to pH 2.5 has been observed for the negatively charged carboxymethyl-b-CD [15], the present study was conducted in order to investigate the chiral separation of dipeptides and tripeptides at pH 5.3 using randomly sulfated b-CD (S-b-CD), as well as the single isomer CDs developed by Vigh and coworkers, heptakis-6-sulfato-b-CD (HS-b-CD) [21] and heptakis-(2,3-diacetyl-6-sulfato)b-CD (HDAS-b-CD) [22].…”

Section: Rizzi and Kremsermentioning

confidence: 99%

Migration order of dipeptide and tripeptide enantiomers in the presence of single isomer and randomly sulfated cyclodextrins as a function of pH

2003

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The present study was conducted in order to evaluate the cyclodextrin (CD)-mediated chiral separation of peptide enantiomers as uncharged analytes at pH 5.3 using randomly sulfated beta-cyclodextrin, heptakis-6-sulfato-beta-CD and heptakis-(2,3-diacetyl-6-sulfato)-beta-CD as chiral selectors. Although less effective compared to stronger acidic conditions, the CDs proved to be suitable chiral selectors for the present set of peptides at pH 5.3. The carrier ability of the negatively charged CDs upon reversal of the applied voltage may also be exploited leading to a reversal of the migration order. In addition, reversal of the enantiomer migration order upon increasing the buffer pH from 2.5 to 5.3 was also observed for Ala-Tyr in the presence of randomly sulfated beta-CD, for Ala-Phe, Ala-Tyr, Phe-Phe, Asp-PheNH(2) and Gly-Ala-Phe in the presence of heptakis-6-sulfato-beta-CD, and for Phe-Phe and Ala-Leu in the presence of heptakis-(2,3-diacetyl-6-sulfato)-beta-CD. The migration behavior could be explained on the basis of the complexation constants and the mobilities of the peptide-CD complexes. While a change in the affinity pattern of the CDs upon increasing the pH was observed for some peptides, complex mobility was the primary factor for other peptide-CD combinations affecting the enantiomer migration order at the two pH values studied.

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Studies on the chiral recognition of peptide enantiomers by neutral and sulfated β-cyclodextrin and heptakis-(2,3-di-O-acetyl)-β-cyclodextrin using capillary electrophoresis and nuclear magnetic resonance

Cited by 45 publications

References 27 publications

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

Enantiomer migration order in chiral capillary electrophoresis

Migration order of dipeptide and tripeptide enantiomers in the presence of single isomer and randomly sulfated cyclodextrins as a function of pH

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