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Intramolecular transformation of an antifungal antibiotic nystatin A 1 into its isomer, iso ‐nystatin A 1 – structural and molecular modeling studies

2016; Wiley; Volume: 54; Issue: 12 Linguagem: Inglês

10.1002/mrc.4478

1097-458X

Katarzyna Szwarc, Marcin Płosiński, Karolina Czerniejewska, Tomasz Laskowski, Arkadiusz Leniak, Jacek Czub, Paweł Kubica, Paweł Sowiński, Jan Pawlak, E. Borowski,

Glycosylation and Glycoproteins Research

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.