title: Toward Structural Correctness: Aquatolide and the Importance of 1D Proton NMR FID Archiving.
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, this study represents a significant contribution to best practices in NMR-based structural analysis and dereplication.
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy and Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Guido F
authors.initials: GF
authors.lastname: Pauli
authors.affiliation: PERCH Solutions Limited , Puijonkatu 24B5, 70110 Kuopio, Finland.
authors.forename: Matthias
authors.initials: M
authors.lastname: Niemitz
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy and Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Bisson
authors.affiliation: Physical Science Department, Butte College , Oroville, California 95965, United States.
authors.forename: Michael W
authors.initials: MW
authors.lastname: Lodewyk
authors.affiliation: Department of Chemistry, University of California-Davis , One Shields Avenue, Davis, California 95616, United States.|Federal University of Santa Catarina , Centro de Curitibanos, Rod. Ulysses Gaboardi, Km 3, Curitibanos, SC 89520-000, Brazil.
authors.forename: Cristian
authors.initials: C
authors.lastname: Soldi
authors.affiliation: Department of Chemistry, University of California-Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
authors.affiliation: Department of Chemistry, University of California-Davis , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Jordy M
authors.initials: JM
authors.lastname: Saya
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Klaas
authors.initials: K
authors.lastname: Vos
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Roel A
authors.initials: RA
authors.lastname: Kleinnijenhuis
authors.affiliation: Van't Hoff Institute for Molecular Sciences, University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.
authors.forename: Henk
authors.initials: H
authors.lastname: Hiemstra
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy and Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: Shao-Nong
authors.initials: SN
authors.lastname: Chen
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy and Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: James B
authors.initials: JB
authors.lastname: McAlpine
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy and Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago , 833 South Wood Street, Chicago, Illinois 60612, United States.
authors.forename: David C
authors.initials: DC
authors.lastname: Lankin
authors.affiliation: Physical Sciences Department, Rosary College of Arts and Sciences, Dominican University , 7900 West Division Street, River Forest, Illinois 60305, United States.
authors.forename: J Brent
authors.initials: JB
authors.lastname: Friesen
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003903:Deuterium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011522:Protons; D012717:Sesquiterpenes / Q000737:chemistry*
chemical_list: D001643:Bridged Bicyclo Compounds; D011522:Protons; D012717:Sesquiterpenes; C580554:aquatolide; D003903:Deuterium
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