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Separation of rotamers of 5-nitrosopyrimidines and estimation of binding constants of their complexes with β-cyclodextrin by capillary electrophoresis.
- Source :
-
Journal of chromatography. A [J Chromatogr A] 2018 Oct 05; Vol. 1570, pp. 164-171. Date of Electronic Publication: 2018 Aug 01. - Publication Year :
- 2018
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Abstract
- For the first time, capillary electrophoresis has been successfully employed for the fast and highly efficient separations of a novel type of stereoisomers - planar rotamers (planamers) of four newly synthesized 5-nitrosopyrimidine derivatives. These derivatives can form two rotamers differing in the orientation of nitroso group due to strong intramolecular hydrogen bonds. Partial separation of rotamers of two 5-nitrosopyrimidines was achieved in alkaline 50 mM sodium tetraborate, pH 9.3, and in acidic 18.5/42 mM Tris/phosphate, pH 2.3, background electrolytes (BGEs) free of stereoselectors. To improve the separation of these rotamers and to attain the baseline or better separation of rotamers of other two 5-nitrosopyrimidines, various BGEs and different cyclodextrins-based stereoselectors were tested. The most effective, i.e. the fastest and baseline or better separations of rotamers of all analyzed 5-nitrosopyrimidines were achieved within a short time, 3.7-9.3 min, in the above alkaline or acidic BGEs using β-cyclodextrin (β-CD) or carboxymethyl-β-CD as stereoselectors. Moreover, since the experiments with β-CD resulted in good separations of rotamers of all the investigated 5-nitrosopyrimidines, the apparent binding constants of their complexes with this selector were determined from the dependence of their effective mobilities on the β-CD concentration in the BGEs. The examined complexes were found to be relatively weak, with the apparent binding constants in the range 11.3-153.0 L/mol.<br /> (Copyright © 2018 Elsevier B.V. All rights reserved.)
- Subjects :
- Electrolytes
Hydrogen Bonding
Hydrogen-Ion Concentration
Nitroso Compounds analysis
Nitroso Compounds isolation & purification
Pyrimidines analysis
Pyrimidines isolation & purification
Stereoisomerism
Electrophoresis, Capillary methods
Nitroso Compounds chemistry
Pyrimidines chemistry
beta-Cyclodextrins chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1873-3778
- Volume :
- 1570
- Database :
- MEDLINE
- Journal :
- Journal of chromatography. A
- Publication Type :
- Academic Journal
- Accession number :
- 30082126
- Full Text :
- https://doi.org/10.1016/j.chroma.2018.07.083