Evaluation of the macrocyclic glycopeptide A-40,926 as a high-performance liquid chromatographic chiral selector and comparison with teicoplanin chiral stationary phase
| Autor: | John P. Kullman, Francesco Gasparrini, Daniel W. Armstrong, Domenico Misiti, Timothy Yu, Angelo Carotti, Ilaria D'Acquarica, Alain Berthod |
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| Rok vydání: | 2000 |
| Předmět: |
Stereochemistry
lc Stereoisomerism Ring (chemistry) Biochemistry antibiotics a-40 Analytical Chemistry Stereocenter chemistry.chemical_compound medicine Imide Chromatography High Pressure Liquid amino acids chiral stationary phases Chromatography Teicoplanin Organic Chemistry Enantioselective synthesis General Medicine Glycopeptide Anti-Bacterial Agents chemistry Evaluation Studies as Topic Spectrophotometry Ultraviolet enantiomer separation Enantiomer teicoplanin medicine.drug |
| Zdroj: | Journal of Chromatography A. 897:113-129 |
| ISSN: | 0021-9673 |
| DOI: | 10.1016/s0021-9673(00)00804-9 |
| Popis: | A new macrocyclic antibiotic of the vancomycin family, referred to by its industrial designation as A-40,926, was bonded to 5 microm silica particles and utilised as a chiral stationary phase (CSP). Since A-40,926 is structurally related to teicoplanin, the A-40,926 CSP was compared to a commercially available teicoplanin CSP. A set of 28 chiral compounds, including amino-acids and related compounds, compounds with a ring containing the stereogenic centre, compounds bearing aromatic structures near their stereogenic centres and alcohols, was tested for enantioseparation on the two CSPs. The results are compared and discussed in terms of enantioselective Gibbs energy difference. The A-40,926 CSP was able to resolve one compound that was not resolved by the teicoplanin CSP. However, it could not separate four compounds that the teicoplanin CSP did separate. It is shown that the A-40,926 CSP is complementary to the teicoplanin CSP, thereby enlarging the number of enantiomers that can be separated by the macrocyclic glycopeptide based CSPs. |
| Databáze: | OpenAIRE |
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