Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation
Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation
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DOI：
10.1021/jo070302k
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发表时间：
2007-06-22
影响因子：
3.6
通讯作者：
Cosimelli, B.
中科院分区：
文献类型：
--
作者：
Stephens, P. J.;Devlin, F. J.;Cosimelli, B.
手性恶二唑-3-酮2最近显示出心肌钙进入通道阻断活性，显著高于地尔硫卓。为了确定该活性的对映体选择性，使用手性色谱法拆分了2的对映体。2的绝对构型（AC）已确定通过比较其振动圆二色性（VCD）光谱，电子圆二色性（ECD）光谱和旋光度（OR）的密度泛函理论（DFT）计算实验VCD，ECD和OR数据。所有三种手性光学性质产生相同的AC; 2的AC被明确地确定为S（+）/R（-）。
The chiral oxadiazol-3-one 2 has recently been shown to exhibit myocardial calcium entry channel blocking activity, substantially higher than that of diltiazem. To determine the enantioselectivity of this activity, the enantiomers of 2 have been resolved using chiral chromatography. The absolute configuration (AC) of 2 has been determined by comparison of density functional theory (DFT) calculations of its vibrational circular dichroism (VCD) spectrum, electronic circular dichroism (ECD) spectrum, and optical rotation (OR) to experimental VCD, ECD, and OR data. All three chiroptical properties yield identical ACs; the AC of 2 is unambiguously determined to be S(+)/R(-).