Unequivocal 13C NMR assignment of cyclohexadienyl rings in bromotyrosine-derived metabolites from marine sponges
Copyright © 2012 John Wiley & Sons, Ltd.
| Publié dans: | Magnetic resonance in chemistry : MRC. - 1985. - 50(2012), 11 vom: 04. Nov., Seite 749-54 |
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| Auteur principal: | |
| Autres auteurs: | , |
| Format: | Article en ligne |
| Langue: | English |
| Publié: |
2012
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| Accès à la collection: | Magnetic resonance in chemistry : MRC |
| Sujets: | Journal Article Research Support, Non-U.S. Gov't Carbon Isotopes Cyclohexenes bromotyrosine Tyrosine 42HK56048U |
| Résumé: | Copyright © 2012 John Wiley & Sons, Ltd. Bromotyrosine-derived compounds are commonly isolated from Verongida sponges and are a major class of marine natural products. Here we report on the unequivocal (13)C NMR assignment of the brominated carbons at positions C-2 and C-4 of the cyclohexadiene ring, two carbons whose resonances are often incorrectly assigned. Interpretation of HMBC data acquired for a series of known bromotyrosine analogues, which included ianthesine E(1), aerothionin (2), 11-hydroxyaerothionin (3), and 11,19-dideoxyfistularin-3 (4), allowed us to unequivocally assign the carbons in question, C-2 and C-4, through the observance of unique HMBC correlations from the C-1 hydroxyl proton. Here we present the complete 2D NMR data sets recorded in DMSO-d(6) for 2-4 that were used to confirm the assignment and establish the working model. Using this model, a survey of the literature revealed that many members of this structure class had been wrongly assigned. This paper serves to reassign those compounds whose (13)C NMR assignment at positions C-2 and C-4 of the cyclohexadiene ring should be reversed |
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| Description: | Date Completed 05.08.2013 Date Revised 21.11.2013 published: Print-Electronic Citation Status MEDLINE |
| ISSN: | 1097-458X |
| DOI: | 10.1002/mrc.3868 |