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Confirmation of the absolute configuration of Stachybotrin C using single-crystal X-ray diffraction analysis of its 4-bromobenzyl ether derivative.
The Journal of Antibiotics ( IF 2.1 ) Pub Date : 2018-Jun-01 , DOI: 10.1038/s41429-018-0042-2
Yu Kuroda , Keiko Hasegawa , Keiichi Noguchi , Kazuhiro Chiba , Keiji Hasumi , Yoshikazu Kitano

The absolute configuration of Stachybotrin C was confirmed in this study. After synthesizing the dimethyl ethers of Stachybotrin C, the C-8 epimer was analyzed by 1D NOESY. However, the stereochemistry determination was difficult through the NOE correlations. Instead, the di(4-bromobenzyl) ether of Stachybotrin C was derived and used for X-ray diffraction analysis, because its single crystal was easier to obtain than that of the original Stachybotrin C. The stereochemistry of Stachybotrin C was determined to be (8S, 9R). This derivatization approach may also be used to prepare single crystals of the analogues.

中文翻译:

使用其4-溴苄基醚衍生物的单晶X射线衍射分析确定水苏蛋白C的绝对构型。

这项研究证实了水苏蛋白C的绝对构型。合成水飞蓟宾C的二甲醚后,通过一维NOESY分析C-8差向异构体。然而,通过NOE相关性难以确定立体化学。相反,因为其单晶比原始的Stachybotrin C更容易获得,所以获得了Stachybotrin C的二(4-溴苄基)醚并用于X射线衍射分析.Stachybotrin C的立体化学被确定为( 8S,9R)。这种衍生化方法也可以用于制备类似物的单晶。
更新日期:2018-03-20
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