Planta Med 2016; 82(S 01): S1-S381
DOI: 10.1055/s-0036-1596120
Abstracts
Georg Thieme Verlag KG Stuttgart · New York

Determination of the absolute configuration of the pseudo-symmetric natural product elatenyne by the crystalline sponge method

S Urban
1   School of Science (Discipline of Chemistry), RMIT University, GPO Box 2476, 3001 Melbourne, Australia
,
R Brkljača
1   School of Science (Discipline of Chemistry), RMIT University, GPO Box 2476, 3001 Melbourne, Australia
,
M Hoshino
2   Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, 113 – 8656 Tokyo, Japan
,
S Lee
2   Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, 113 – 8656 Tokyo, Japan
,
M Fujita
2   Department of Applied Chemistry, School of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, 113 – 8656 Tokyo, Japan
› Author Affiliations
Further Information

Publication History

Publication Date:
14 December 2016 (online)

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    The determination of the absolute structure of natural products presents a major structural challenge, particularly for oily compounds that preclude analysis via X-ray crystallography. Elatenyne is an oily dibrominated marine natural product which was isolated in 1986 [1].

    Despite its simple 2,2'-bifuranyl backbone, its relative structure was only recently determined [2]. In this work, the absolute structure of natural elatenyne was unveiled on the microgram scale 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 [3]. The total amount required for the experiments was only approximately 100 µg, and the majority of this (95 µg) could be recovered after the experiments. The study represents the first real application of the crystalline sponge method to the determination of the absolute configuration of a natural product.

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    This presentation will provide an overview of the study and outline the impact for natural product isolation and structure determination.

    Acknowledgements: The research was supported by the ACCEL project of the Japan Science and Technology Agency (JST) with M.F. as the principle investigator.

    Keywords: crystalline sponge, absolute configuration, natural product, X-ray crystallography.

    References:

    [1] Hall JG, Reiss JA. Elatenyne – a pyrano[3,2,B]pyranyl vinyl acetylen from the red alga Laurencia elata. Aust J Chem 1986; 39: 1401 – 1409

    [2] Dyson BS, Burton JW, Sohn T, Kim B, Bae H, Kim D. Total synthesis and structure confirmation of elatenyne: Success of computational methods for NMR prediction with highly flexible diastereomers. J Am Chem Soc 2012; 134: 11781 – 11790

    [3] Urban S, Brkljača R, Hoshino M, Lee S, Fujita M. Determination of the absolute configuration of the pseudo-symmetric natural product elatenyne by the crystalline sponge method. Angew Chem Int Ed 2016; DOI 10.1002/anie.201509761


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    No conflict of interest has been declared by the author(s).

     
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