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

The Journal of Organic Chemistry
Guido F PauliJ Brent Friesen

Abstract

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 (1)H 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 (1)H spectra encode a wealth of information about bonds and molecular geometry that may be fully mined by (1)H iterative full spin analysis (HiFSA). Fully characterized 1D (1)H 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...Continue Reading

References

Jul 1, 2011·Bioorganic & Medicinal Chemistry·Takashi L SuyamaKerry L McPhail
Aug 24, 2011·Journal of Natural Products·Gloria M Molina-SalinasNoemí Waksman
Aug 15, 2012·Journal of Cheminformatics·Marcus D HanwellGeoffrey R Hutchison
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Mar 7, 2013·The Journal of Organic Chemistry·José G NapolitanoGuido F Pauli
Sep 7, 2013·The Journal of Organic Chemistry·José G NapolitanoGuido F Pauli
Apr 9, 2014·The Journal of Organic Chemistry·R Thomas WilliamsonTeodor Parella
May 21, 2014·Organic Letters·Naoki TerayamaShinji Nagumo
Jun 5, 2014·Journal of Natural Products·Guido F PauliMatthias Niemitz
Oct 9, 2014·Journal of Medicinal Chemistry·Guido F PauliJosé G Napolitano
Nov 20, 2014·Organic Letters·Wei GaoGuido F Pauli
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Jul 18, 2015·Organic Letters·Jordy M SayaHenk Hiemstra

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Citations

Sep 10, 2016·Organic Letters·D Sai Reddy, Andrei G Kutateladze
Oct 19, 2016·Magnetic Resonance in Chemistry : MRC·Julien Wist
Dec 4, 2016·Bioorganic & Medicinal Chemistry Letters·Paul OguadinmaSteven R LaPlante
May 21, 2016·Natural Product Reports·Jonathan BissonGuido F Pauli
Mar 28, 2018·Magnetic Resonance in Chemistry : MRC·Luc PatinyJulien Wist
Oct 6, 2017·Magnetic Resonance in Chemistry : MRC·Luc PatinyJulien Wist
Jul 13, 2017·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Prasad L PolavarapuVijay Raghavan
Apr 4, 2021·International Journal of Molecular Sciences·Jiří Czernek, Jiří Brus
Aug 5, 2017·Journal of Natural Products·Elda M Melchor-MartínezVerónica M Rivas-Galindo
Feb 13, 2018·Journal of Natural Products·Nada IbrahimJean-Marc Nuzillard
Oct 17, 2017·Journal of Natural Products·Wei GaoGuido F Pauli
Jun 19, 2018·The Journal of Organic Chemistry·Andrei G KutateladzeTina Holt
Dec 17, 2016·Organic Letters·Nicolás GrimblatAriel M Sarotti

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Methods Mentioned

BETA
NMR
X-ray
2D

Software Mentioned

Avogadro
Free
QuILTs
LAOCOON
PERCH
jVisualizer
QuILT
HiFSA
Free Software

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