Chiral Separation of α-Amino Acid Derivatives by Capillary Electrophoresis Using 6-Amino-6-deoxy-ß-cyclodextrin and Its N-Hexyl Derivative as Chiral Selectors

Egashira, Naoyoshi; Mutoh, Osamu; Kurauchi, Yoshiaki; Ohga, Kazuya

doi:10.2116/analsci.12.503

Cited by 19 publications

(3 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These data are in accordance with those obtained with mono(6-amino-6-deoxy)-b-CD [20]. Surprisingly, the introduction of hydroxyethyl groups in primary amino groups (heptakis(6-hydroxyethylamino-6-deoxy)-b-CD as a chiral selector) allows to achieve the good enantioseparation of dansyl-Asp [12].…”

Section: Separation Of Amino Acid Derivativessupporting

confidence: 89%

Heptakis(6‐amino‐6‐deoxy)‐β‐cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis

Budanova¹,

Shapovalova²,

Lopatin³

et al. 2004

Electrophoresis

View full text Add to dashboard Cite

A hepta-substituted beta-cyclodextrin bearing seven amino groups, heptakis(6-amino-6-deoxy)-beta-cyclodextrin (per-6-NH2-beta-CD) was successfully used as a chiral selector for the enantioseparation of different anionic analytes. The running buffer pH and chiral selector concentration were the studied parameters crucial in achieving the maximum possible enantioresolution. Enantiomeric separation of a mixture of seven carboxybenzyl-amino acids was achieved in 24 min. Excellent resolution was obtained for carboxybenzyl-tryptophan (Rs = 11.2).

show abstract

Section: Separation Of Amino Acid Derivativessupporting

confidence: 89%

Heptakis(6‐amino‐6‐deoxy)‐β‐cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis

Budanova¹,

Shapovalova²,

Lopatin³

et al. 2004

Electrophoresis

View full text Add to dashboard Cite

show abstract

“…As a result, the stability of the inclusion complex formed between positively charged CD and oppositely charged analyte enantiomers will be increased due to the electrostatic interaction. Thus, the chiral resolution should be enhanced in comparison with that achieved with native b-CD [24]. However, a further increasing of pH led to a general decrease in resolution.…”

Section: Effect Of Ph On the Separationmentioning

confidence: 98%

Chiral separation of dansyl amino acids in capillary electrophoresis using mono‐(3‐methyl‐imidazolium)‐β‐cyclodextrin chloride as selector

Tang¹,

Ong²,

Ng³

2007

J of Separation Science

View full text Add to dashboard Cite

Enantioseparations of fourteen dansyl amino acids were achieved by using a positively-charged single-isomer beta-cyclodextrin, mono-(3-methyl-imidazolium)-beta-cyclodextrin chloride, as a chiral selector. Separation parameters such as buffer pH, selector concentration, separation temperature, and organic modifier were investigated for the enantioseparation in order to achieve the maximum possible resolution. Chiral separation of dansyl amino acids was found to be highly dependent on pH since the degree of protonation of these amino acids can alter the strength of electrostatic interaction and/or inclusion complexation between each enantiomer and chiral selector. In general, the chiral resolution of dansyl amino acids was enhanced at higher pH, which indicates that the carboxylate group on the analytes may interact with the imidazolium group of cationic cyclodextrin. For most analytes, a distinct maximum in enantioresolution was obtained at pH 8.0. Moreover, the chiral separation can be further improved by careful tuning of the separation parameters such as higher selector concentration (e.g. 10 mM), lower temperature, and addition of methanol. Enantioseparation of a standard mixture of these dansyl amino acids was further achieved in a single run within 30 min.

show abstract

“…Figure 9 illustrates the simultaneous chiral separation of 13 FMOC-AAs. Egashira and co-workers [83] prepared two CD derivatives, 6-amino-6-deoxy-f3-cyclodextrin (ACD) and 6-deoxy-6-hexylamino-~-cyclodextrin Examples of the resolving power achieved with these combinations is illustrated in Fig. 10.…”

Section: Chiral Selectors Abbreviationmentioning

confidence: 99%

Developments in amino acid analysis using capillary electrophoresis

Smith

1997

Electrophoresis

View full text Add to dashboard Cite

The current status in the analysis of amino acids using capillary electrophoresis is addressed. This area of biological analysis has received increased attention with more than 200 articles being published in the last five years. This review discusses pre-, post-, and on-column derivatization techniques used to tag amino acids providing a detectable moiety. Several separation methodologies which provided resolution for large sets of amino acids are presented. An overview of advances in the enantiomeric resolution methodologies for amino acids is given. Both direct and indirect enantiomeric separation schemes are summarized. Recent advances in detection strategies for both derivatized and underivatized amino acids are presented. Applications utilizing amino acid analysis by capillary electrophoresis are described. This review covers articles published between 1991 and 1996.

show abstract

Chiral Separation of α-Amino Acid Derivatives by Capillary Electrophoresis Using 6-Amino-6-deoxy-ß-cyclodextrin and Its N-Hexyl Derivative as Chiral Selectors

Cited by 19 publications

References 13 publications

Heptakis(6‐amino‐6‐deoxy)‐β‐cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis

Heptakis(6‐amino‐6‐deoxy)‐β‐cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis

Chiral separation of dansyl amino acids in capillary electrophoresis using mono‐(3‐methyl‐imidazolium)‐β‐cyclodextrin chloride as selector

Developments in amino acid analysis using capillary electrophoresis

Contact Info

Product

Resources

About