title: Intramolecular transformation of an antifungal antibiotic nystatin A1into its isomer, iso-nystatin A1- structural and molecular modeling studies.
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 A1with 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.
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Szwarc
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Płosiński
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Karolina
authors.initials: K
authors.lastname: Czerniejewska
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Laskowski
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.
authors.forename: Arkadiusz
authors.initials: A
authors.lastname: Leniak
authors.affiliation: Department of Physical Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Jacek
authors.initials: J
authors.lastname: Czub
authors.affiliation: Department of Analytical Chemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Paweł
authors.initials: P
authors.lastname: Kubica
authors.affiliation: Międzyuczelniane Laboratorium Magnetycznego Rezonansu Jądrowego, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Paweł
authors.initials: P
authors.lastname: Sowiński
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Jan
authors.initials: J
authors.lastname: Pawlak
authors.affiliation: Department of Pharmaceutical Technology and Biochemistry, Faculty of Chemistry, Gdansk University of Technology, Gdansk, Poland.
authors.forename: Edward
authors.initials: E
authors.lastname: Borowski
mesh_terms: D000935:Antifungal Agents / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D007536:Isomerism; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D056004:Molecular Dynamics Simulation; D009761:Nystatin / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: D000935:Antifungal Agents; D007783:Lactones; D009761:Nystatin
keywords: 13C; 1H; NMR; iso-nystatin A1; isomeric form; molecular modeling; nystatin A1; translactonization