High-performance liquid chromatographic chiral separation of β2-homoamino acids

Zoltán Pataj, R. Berkecz, I. Ilisz, Aleksandra Misicka, Dagmara Tymecka, F. Fülöp, Daniel W. Armstrong, A. Péter

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45°C and the changes in enthalpy, Δ(ΔH°) , entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The -Δ(ΔG°) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of β2-homoamino acids with branched alkyl or aryl side-chains, whereas for β2-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R <S.

Original languageEnglish
Pages (from-to)787-798
Number of pages12
JournalChirality
Volume21
Issue number9
DOIs
Publication statusPublished - Oct 2009

Fingerprint

Enantiomers
Phase composition
Acids
Liquids
Teicoplanin
Temperature
Glycopeptides
Entropy
Sugars
Peptides
Free energy
Enthalpy
chirobiotic T
teicoplanin aglycone

Keywords

  • B2-homoamino acids
  • Chirobiotic columns
  • Column liquid chromatography
  • Macrocyclic glycopeptide-based chiral stationary phases

ASJC Scopus subject areas

  • Organic Chemistry
  • Analytical Chemistry
  • Drug Discovery
  • Pharmacology
  • Catalysis
  • Spectroscopy

Cite this

High-performance liquid chromatographic chiral separation of β2-homoamino acids. / Pataj, Zoltán; Berkecz, R.; Ilisz, I.; Misicka, Aleksandra; Tymecka, Dagmara; Fülöp, F.; Armstrong, Daniel W.; Péter, A.

In: Chirality, Vol. 21, No. 9, 10.2009, p. 787-798.

Research output: Contribution to journalArticle

Pataj, Zoltán ; Berkecz, R. ; Ilisz, I. ; Misicka, Aleksandra ; Tymecka, Dagmara ; Fülöp, F. ; Armstrong, Daniel W. ; Péter, A. / High-performance liquid chromatographic chiral separation of β2-homoamino acids. In: Chirality. 2009 ; Vol. 21, No. 9. pp. 787-798.
@article{008a4661ae2345f98167d0acb6b59161,
title = "High-performance liquid chromatographic chiral separation of β2-homoamino acids",
abstract = "Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45°C and the changes in enthalpy, Δ(ΔH°) , entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The -Δ(ΔG°) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of β2-homoamino acids with branched alkyl or aryl side-chains, whereas for β2-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R <S.",
keywords = "B2-homoamino acids, Chirobiotic columns, Column liquid chromatography, Macrocyclic glycopeptide-based chiral stationary phases",
author = "Zolt{\'a}n Pataj and R. Berkecz and I. Ilisz and Aleksandra Misicka and Dagmara Tymecka and F. F{\"u}l{\"o}p and Armstrong, {Daniel W.} and A. P{\'e}ter",
year = "2009",
month = "10",
doi = "10.1002/chir.20670",
language = "English",
volume = "21",
pages = "787--798",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "9",

}

TY - JOUR

T1 - High-performance liquid chromatographic chiral separation of β2-homoamino acids

AU - Pataj, Zoltán

AU - Berkecz, R.

AU - Ilisz, I.

AU - Misicka, Aleksandra

AU - Tymecka, Dagmara

AU - Fülöp, F.

AU - Armstrong, Daniel W.

AU - Péter, A.

PY - 2009/10

Y1 - 2009/10

N2 - Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45°C and the changes in enthalpy, Δ(ΔH°) , entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The -Δ(ΔG°) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of β2-homoamino acids with branched alkyl or aryl side-chains, whereas for β2-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R <S.

AB - Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural β2-homoamino acids on chiral stationary phases containing macrocyclic glycopeptides (teicoplanin-containing Chirobiotic T and T2) or the macrocyclic peptide teicoplanin aglycone (Chirobiotic TAG) as chiral selectors. The effects of the organic modifier, the mobile phase composition, temperature, and the structures of the analytes on the separations were investigated. Separations were carried out at constant mobile phase compositions in temperature range 7-45°C and the changes in enthalpy, Δ(ΔH°) , entropy, Δ(ΔS°), and free energy, Δ(ΔG°), were calculated. The -Δ(ΔG°) values obtained on the three columns indicated that Chirobiotic TAG, without sugar units, may promote the interactions of the enantiomers of β2-homoamino acids with branched alkyl or aryl side-chains, whereas for β2-homoamino acids with alkyl side-chains Chirobiotic T and T2 seem to be more favorable. The elution sequence was determined in some cases and was observed to be R <S.

KW - B2-homoamino acids

KW - Chirobiotic columns

KW - Column liquid chromatography

KW - Macrocyclic glycopeptide-based chiral stationary phases

UR - http://www.scopus.com/inward/record.url?scp=70350537610&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=70350537610&partnerID=8YFLogxK

U2 - 10.1002/chir.20670

DO - 10.1002/chir.20670

M3 - Article

C2 - 18979532

AN - SCOPUS:70350537610

VL - 21

SP - 787

EP - 798

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 9

ER -