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Review
. 2011 Nov 15;19(22):6675-701.
doi: 10.1016/j.bmc.2011.06.011. Epub 2011 Jun 12.

Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis

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Review

Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis

Takashi L Suyama et al. Bioorg Med Chem. .

Abstract

The structural assignment of new natural product molecules supports research in a multitude of disciplines that may lead to new therapeutic agents and or new understanding of disease biology. However, reports of numerous structural revisions, even of recently elucidated natural products, inspired the present survey of techniques used in structural misassignments and subsequent revisions in the context of constitutional or configurational errors. Given the comparatively recent development of marine natural products chemistry, coincident with modern spectroscopy, it is of interest to consider the relative roles of spectroscopy and chemical synthesis in the structure elucidation and revision of those marine natural products that were initially misassigned. Thus, a tabulated review of all marine natural product structural revisions from 2005 to 2010 is organized according to structural motif revised. Misassignments of constitution are more frequent than perhaps anticipated by reliance on HMBC and other advanced NMR experiments, especially when considering the full complement of all natural products. However, these techniques also feature prominently in structural revisions, specifically of marine natural products. Nevertheless, as is the case for revision of relative and absolute configuration, total synthesis is a proven partner for marine, as well as terrestrial, natural products structure elucidation. It also becomes apparent that considerable 'detective work' remains in structure elucidation, in spite of the spectacular advances in spectroscopic techniques.

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Figures

Figure 1
Figure 1
A. Numbers of all natural products misassigned per 5-year period; B. Numbers of marine natural products misassigned per 5-year period.
Figure 2
Figure 2
A. Techniques used in the misassignment of all natural product structures revised during 2005 – 2010; B. Techniques used in the misassignment of marine natural product structures revised during 2005 – 2010. Piechart key: NOE – NOE, NOESY, ROESY; Comparison – NMR comparison; J-based – coupling constant analysis; Other NMR – mostly 1D NMR, but includes COSY, HSQC, etc; MS – any MS technique except LC-MS; Derivatization – Marfey’s, Mosher’s, peptide hydrolysis, chemical correlation; CD/OR – circular dichroism or optical rotation; Model – any computational modeling; Chromatog – any TLC identification to HPLC (often in combination with “Derivatization”); Other tech – IR, UV, biosynthetic considerations, etc; Synthesis – any of partial synthesis, model synthesis, semi-synthesis.
Figure 3
Figure 3
A. Techniques used in the detection and revision of all natural product structures (2005 – 2010); B. Techniques used in the detection and revision of marine natural product structures (2005 – 2010).
Figure 4
Figure 4
Misassigned marine natural product structures not yet revised (detected 2005 – 2010).

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