کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5417390 | 1506929 | 2009 | 9 صفحه PDF | دانلود رایگان |
عنوان انگلیسی مقاله ISI
Comparative study of patulin, ascladiol, and neopatulin by density functional theory
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کلمات کلیدی
موضوعات مرتبط
مهندسی و علوم پایه
شیمی
شیمی تئوریک و عملی
پیش نمایش صفحه اول مقاله
چکیده انگلیسی
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++Gââ level of theory. Both aqueous solvation studies using a continuum solvation model and in vacuo calculations resulted in several geometry optimized conformations of patulin within a range 2Â kcal/mol. One conformation for each enantiomer was preferred by â¼1Â kcal/mol over the other geometry optimized conformations considered. Similar results were found for neopatulin. Multiple conformations of ascladiol possessed favorable intramolecular hydrogen bond interactions. The B3LYP/6-311++Gââ results are in agreement with experimentally observed crystallographic data for patulin, and suggest several conformations may be important for structure-activity studies of this mycotoxin and its precursors.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure: THEOCHEM - Volume 894, Issues 1â3, 30 January 2009, Pages 23-31
Journal: Journal of Molecular Structure: THEOCHEM - Volume 894, Issues 1â3, 30 January 2009, Pages 23-31
نویسندگان
Michael Appell, Mary Ann Dombrink-Kurtzman, David F. Kendra,