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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
Author(s) -
Szwarc Katarzyna,
Płosiński Marcin,
Czerniejewska Karolina,
Laskowski Tomasz,
Leniak Arkadiusz,
Czub Jacek,
Kubica Paweł,
Sowiński Paweł,
Pawlak Jan,
Borowski Edward
Publication year - 2016
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4478
Subject(s) - chemistry , nystatin , intramolecular force , polyene , stereochemistry , computational chemistry , ring (chemistry) , molecule , antifungal , antibiotics , organic chemistry , biochemistry , microbiology and biotechnology , biology
Nystatin A 1 , 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 A 1 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.