Intramolecular transformation of an antifungal antibiotic nystatin A1 into its isomer,iso‐nystatin A1 – structural and molecular modeling studies |
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Authors: | Katarzyna Szwarc Marcin P?osiński Karolina Czerniejewska Tomasz Laskowski Arkadiusz Leniak Jacek Czub Pawe? Kubica Pawe? Sowiński Jan Pawlak Edward Borowski |
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Affiliation: | 1. Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland;2. Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland;3. Department of Physical Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland;4. Department of Analytical Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland;5. Mi?dzyuczelniane Laboratorium Magnetycznego Rezonansu J?drowego, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland |
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Abstract: | Nystatin A1, a polyene macrolide antifungal antibiotic, in a slightly basic or acidic solution undergoes an intramolecular transformation, yielding a structural isomer, the translactonization product, iso‐nystatin A1 with lactone ring diminished by two carbon atoms. Structural evidence is provided by advanced NMR and Mass Spectrometry (MS) studies. Molecular dynamics simulations and quantum mechanics calculations gave the insight into the course and mechanism of the transformation and its effect on the conformation of the subject molecule. Copyright © 2016 John Wiley & Sons, Ltd. |
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Keywords: | NMR 1H 13C nystatin A1 translactonization isomeric form iso‐nystatin A1 molecular modeling |
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