RDC-based determination of the relative configuration of the fungicidal cyclopentenone 4,6-diacetylhygrophorone A12..
RDC-based determination of the relative configuration of the fungicidal cyclopentenone 4,6-diacetylhygrophorone A12..
复制标题
DOI：
10.1021/np300728b
复制
发表时间：
2013-05
影响因子：
5.1
通讯作者：
V. Schmidts;Maic Fredersdorf;Tilo Lübken;A. Porzel;N. Arnold;L. Wessjohann;C. Thiele
中科院分区：
文献类型：
--
作者：
V. Schmidts;Maic Fredersdorf;Tilo Lübken;A. Porzel;N. Arnold;L. Wessjohann;C. Thiele
从担子菌属（Hygrophorus）子实体中分离出的环戊烯酮类化合物hydrophorones具有良好的抗真菌活性。虽然用标准核磁共振和质谱技术确定了4,6-二乙酰水酮A(12)(3)的结构和环戊酮环上立体中心的相对构型，但无法确定外环立体中心的相对构型。通过将样品3引入对准介质并测量各向异性核磁共振参数，即残余偶极耦合，我们能够通过将几种结构建议拟合到实验数据中，同时明确确定4,6-二乙酰水酮a（12）中所有三个立体中心的相对构型。
The hygrophorones, a class of cyclopentenones isolated from fruiting bodies of the genus Hygrophorus (basidiomycetes), show promising antifungal activity. While the constitution of 4,6-diacetylhygrophorone A(12) (3) and the relative configuration of the stereogenic centers in the cyclopentenone ring were elucidated using standard NMR and MS techniques, the relative configuration of the exocyclic stereogenic center could not be assigned. By introducing a sample of 3 into an alignment medium and measuring anisotropic NMR parameters, namely, residual dipolar couplings, we were able to unambiguously determine the relative configuration of all three stereogenic centers in 4,6-diacetylhygrophorone A(12) simultaneously by fitting several structure proposals to the experimental data.