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Title:   Author  item
                                            Appell, Michaelitem
                                            Dombrink Kurtzman, Mary Annitem
                                            Kendra, David
  Submitted to: Bioorganic and Medicinal Chemistry
                                    Publication Type: Peer Reviewed Journal
                                    Publication Acceptance Date: 9/22/2008
                                    Publication  Date: 1/30/2009
                                    Citation: Appell, M.D., Dombrink Kurtzman, M., Kendra, D.F. 2009. Comparative Study of Patulin, Ascladiol, and Neopatulin by Density Functional Theory. Journal of Molecular Structure: THEOCHEM. 894(1-3):23-31.Interpretive Summary: Patulin is a small molecule and mycotoxin produced by several fungal species.  Although patulin contamination is most commonly associated with apple rot, it is a potential contaminant of other types of fruit and vegetable products.  Levels of this important mycotoxin are regulated by several countries, including the United States.  Patulin contamination is related to the production of E-ascladiol and neopatulin.  To better understand the chemistry of patulin and the molecules involved in patulin production, a study was carried out on the three dimension structures of these molecules using state-of-the-art calculations.  This study provides important information for understanding the chemistry of patulin production at the molecular level, and will be useful in the design and evaluation of materials that interact with patulin.
                                Technical Abstract: Patulin, a secondary metabolite produced by several fungal species, is a potential contaminant of fruit and vegetable products.  To better understand the structure and electronic properties of this mycotoxin and its biosynthetic precursors, a density functional theory (DFT) study was performed on conformations of patulin, ascladiol, and neopatulin.  Geometry optimization and transition state calculations were carried out using the three parameter B3LYP functional at the 6-311++G** level of theory.  Both aqueous solvation studies using a continuum solvation model and in vacuo calculations resulted in several stable conformations of patulin within a range two kcal/mol.  One conformation was preferred by ~one kcal/mol over the other geometry optimized conformations considered.  Similar results were found for neopatulin.  Ascladiol had several stable conformations within two kcal/mol that possessed favorable intramolecular hydrogen bond interactions.  High level density functional calculations were applied to investigate the conformational preferences of important molecules involved in patulin synthesis, and these results serve as a basis for modeling studies and interpretation of experimental results.


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