School of Applied Sciences (Discipline of Chemistry), RMIT University, GPO Box 2476, Melbourne, 3001, Victoria, Australia.
Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-8656, Japan.
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2678-82. doi: 10.1002/anie.201509761. Epub 2016 Jan 14.
Elatenyne is a marine natural product that was isolated in 1986. Despite its simple 2,2'-bifuranyl backbone, its relative structure was only recently determined. The absolute configuration of elatenyne has still not been unequivocally confirmed because of its pseudo-meso core structure, which results in a specific rotation, [α]D , of almost zero. In this work, the structure of natural elatenyne was determined by the crystalline sponge method and the use of a porous coordination network (a crystalline sponge) capable of absorbing organic guests; in the sponge, the absorbed guests are ordered and crystallographically observable. The crystalline sponge could differentiate between the two very similar alkyl side chains, and the absolute structure of elatenyne was thus reliably determined. The total amount required for the experiments was only approximately 100 μg, and the majority (95 μg) could be recovered after the experiments.
埃拉廷炔是一种海洋天然产物，于 1986 年分离得到。尽管其具有简单的 2,2'-联呋喃骨架，但直到最近才确定其相对结构。由于其具有假内消旋核结构，导致旋光度 [α]D几乎为零，因此埃拉廷炔的绝对构型仍未得到明确证实。在这项工作中，通过晶体海绵法和使用能够吸收有机客体的多孔配位网络（晶体海绵）确定了天然埃拉廷炔的结构；在海绵中，吸收的客体是有序的并且在结晶学上是可观察的。晶体海绵可以区分两个非常相似的烷基侧链，因此可靠地确定了埃拉廷炔的绝对结构。实验所需的总量仅约为 100μg，实验后可回收 95μg 左右。
