کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
10553571 967877 2011 6 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Study on the absolute configuration of levetiracetam via density functional theory calculations of electronic circular dichroism and optical rotatory dispersion
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آنالیزی یا شیمی تجزیه
پیش نمایش صفحه اول مقاله
Study on the absolute configuration of levetiracetam via density functional theory calculations of electronic circular dichroism and optical rotatory dispersion
چکیده انگلیسی
Theoretical calculation of chiroptical properties has been a powerful tool for the absolute configuration assignment of chiral compounds including synthetic drugs and natural products. In the present work, time-dependent density functional theory (TDDFT) calculations of electronic circular dichroism (ECD) and optical rotatory dispersion (ORD) were employed to investigate the absolute configuration of levetiracetam, which is a widely used anticonvulsant drug. Nine conformers were generated by conformation search using the MMFF94 molecular mechanics force field, and the geometries were then optimized using the Becke 3-Lee-Yang-Parr (B3LYP) exchange-correlation functional. The population-averaged ECD spectrum was obtained by adding ECD spectrum of each conformer using Boltzmann statistics. The predicted ECD spectrum is in excellent agreement with the measured ECD spectrum of levetiracetam. Theoretical ORD spectra show the same tendency as the experimental data of levetiracetam, further confirming the absolute configuration derived from the ECD spectra. Our results demonstrated that the only chiral carbon atom of levetiracetam is unambiguously to be S configuration.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Pharmaceutical and Biomedical Analysis - Volume 56, Issue 3, 1 November 2011, Pages 465-470
نویسندگان
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