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📕 Toward Structural Correctness: Aquatolide and the Importance of 1D Proton NMR FID Archiving


Tags: NMR raw data initiative QuILTs news
Pauli GF, Niemitz M, Bisson J, Lodewyk MW, Soldi C, Shaw JT, Tantillo DJ, Saya JM, Vos K, Kleinnijenhuis RA, Hiemstra H, Chen S, McAlpine JB, Lankin DC, Friesen JB
Journal of Organic Chemistry ASAP, xxx-yyy (2016)
DOI:10.1021/acs.joc.5b02456
[OpenAccess]

Abstract

TOC graphic of the aquatolide paper, not the one from the paper

The revision of the structure of the sesquiterpene aquatolide from a bicyclo[2.2.0]hexane to a bicyclo[2.1.1]hexane structure using compelling NMR data, X-ray crystallography, and the recent confirmation via full synthesis exemplify that the achievement of “structural correctness” depends on the completeness of the experimental evidence. Archived FIDs and newly acquired aquatolide spectra demonstrate that archiving and rigorous interpretation of 1D 1H NMR data may enhance the reproducibility of (bio)chemical research and curb the growing trend of structural misassignments. Despite being the most accessible NMR experiment, 1D 1H spectra encode a wealth of information about bonds and molecular geometry that may be fully mined by 1H iterative full spin analysis (HiFSA). Fully characterized 1D 1H spectra are unideterminant for a given structure. The corresponding FIDs may be readily submitted with publications and collected in databases. Proton NMR spectra are indispensable for structural characterization even in conjunction with 2D data. Quantum interaction and linkage tables (QuILTs) are introduced for a more intuitive visualization of 1D J-coupling relationships, NOESY correlations, and heteronuclear experiments. Overall, this study represents a significant contribution to best practices in NMR-based structural analysis and dereplication.