title: Structure and tautomerism of tenuazonic acid--a synergetic computational and spectroscopic approach.
abstract: All reasonable tautomers and rotamers of tenuazonic acid, which is considered to be of the highest toxicity amongst the Alternaria mycotoxins, were investigated by DFT calculations at different levels of theory in gas phase and in solution to obtain optimized geometries for further examinations. Calculated NMR spectra of tautomeric structures are being presented and compared to experimental data to finally achieve a synergetic computational and spectroscopic approach for structure elucidation of 3-acetyltetramic acids, affording the predominant tautomer of tenuazonic acid in aqueous solution. Furthermore we were able to simulate the less hindered rotation of the exocyclic acetyl group, which occurs after dissociation of tenuazonic acid in protic solvents.
authors.affiliation: Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, 1060 Vienna, Austria. hannes.mikula@tuwien.ac.at
authors.forename: Hannes
authors.initials: H
authors.lastname: Mikula
authors.forename: Ernst
authors.initials: E
authors.lastname: Horkel
authors.forename: Philipp
authors.initials: P
authors.lastname: Hans
authors.forename: Christian
authors.initials: C
authors.lastname: Hametner
authors.forename: Johannes
authors.initials: J
authors.lastname: Fröhlich
mesh_terms: D000528:Alternaria / Q000737:chemistry*; D003198:Computer Simulation; D005663:Furans / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry; D013053:Spectrophotometry; D013057:Spectrum Analysis; D013237:Stereoisomerism; D013720:Tenuazonic Acid / Q000737:chemistry*; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
chemical_list: D005663:Furans; D012997:Solvents; D014867:Water; C066006:3-acetyltetramic acid; D013720:Tenuazonic Acid