uu.seUppsala University Publications
Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Reversal of Enantiomeric Retention Order by Using a Single N-Derivatized Dipeptide as Chiral Mobile Phase Additive and Porous Graphitised Carbon as Stationary Phase
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
2007 (English)In: Chromatographia, ISSN 0009-5893, E-ISSN 1612-1112, Vol. 66, no 5-6, 349-356 p.Article in journal (Refereed) Published
Abstract [en]

In this work the three dipeptides, Z-l-alanyl-l-glutaric acid (Z-l-ala-l-glu), Z-l-phenylanyl-l-glutaric acid (Z-l-phe-l-glu) and Z-glycyl-l-glutaric acid (Z-gly-l-glu) were tested as chiral counter ions for enantiomeric resolution of amino alcohols. The influence of solute and counter ion structure upon retention and enantioselectivity was evaluated. The chiral counter ions were dissolved in a mixture of polar solvents, i.e., ethyl acetate, methanol and acetonitrile and the achiral solid phase used was porous graphitic carbon, marketed as Hypercarb. The enantioselectivities observed for the tested solutes were highly influenced by the used chiral counter ion structure. For example no enantioselectivity was observed for (R,S)-alprenolol using Z-l-ala-l-glu while a separation factor (α) of 1.59 was obtained using Z-l-phe-l-glu as chiral counter ion. High selectivity factors (α > 2.7) were observed between enantiomers of tertiary amines using Z-l-phe-l-glu as counter ion. Interestingly, the structure of the counter ion, as well as the charge on Z-l-phe-l-glu and the mobile phase solvent composition, influenced the retention order of the enantiomers.

Place, publisher, year, edition, pages
2007. Vol. 66, no 5-6, 349-356 p.
Keyword [en]
Column liquid chromatography, Hypercarb®, Chiral ion-pair chromatography, Counter ion structure, Amino alcohols
National Category
Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-11589DOI: 10.1365/s10337-007-0352-1ISI: 000249712300007OAI: oai:DiVA.org:uu-11589DiVA: diva2:39358
Available from: 2007-10-04 Created: 2007-10-04 Last updated: 2017-12-11Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full texthttp://www.springerlink.com/content/a37n2pr4362w1760/
By organisation
Analytical Pharmaceutical Chemistry
In the same journal
Chromatographia
Pharmaceutical Sciences

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 385 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf