Title: Investigation of Patulin and its Biosynthetic Precursors by Density Functional Methods Authors
|Dombrink Kurtzman, Mary Ann|
Submitted to: American Chemical Society National Meeting
Publication Type: Abstract Only
Publication Acceptance Date: August 20, 2009
Publication Date: August 20, 2009
Citation: Appell, M.D., Dombrink Kurtzman, M., Kendra, D.F. 2009. Investigation of Patulin and its Biosynthetic Precursors by Density Functional Methods [abstract]. American Chemical Society National Meeting. AGFD 228. Technical Abstract: Production of the toxin patulin by fungi that contaminate fruit and vegetable products is a food safety concern, especially for decaying apples. Reducing exposure to this regulated mycotoxin can be complicated by post-harvest biosynthesis during storage and processing. These biosynthetic pathways are important targets for reducing exposure to naturally occurring toxins. This study applies density functional methods to compare structures and electronic properties of patulin and its co-occurring biosynthetic precursors to aid in analysis. Geometry optimization studies at the B3LYP/6-311++G** level are in agreement with crystallography data for patulin. Conformational preferences of patulin, E-ascladiol, and neopatulin are influenced by the conjugated double system. Both patulin and its precursor neopatulin possess similar conformational trends, including axial preference for the hydroxyl substituent. E-ascladiol conformers are stabilized through several intramolecular hydrogen bonding schemes. Comparing density functional results for patulin with its structurally related biosynthetic precursors identified key intramolecular interactions associated with conformer stabilization.