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231224s2012 xx |||||o 00| ||eng c |
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|a 10.1002/mrc.3868
|2 doi
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|a pubmed25n0736.xml
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|a eng
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|a Kalaitzis, John A
|e verfasserin
|4 aut
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|a Unequivocal 13C NMR assignment of cyclohexadienyl rings in bromotyrosine-derived metabolites from marine sponges
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|c 2012
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|a Text
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|a ƒaComputermedien
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|a ƒa Online-Ressource
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|a Date Completed 05.08.2013
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|a Date Revised 21.11.2013
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|a published: Print-Electronic
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|a Citation Status MEDLINE
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|a Copyright © 2012 John Wiley & Sons, Ltd.
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|a 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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|a Journal Article
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|a Research Support, Non-U.S. Gov't
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|a Carbon Isotopes
|2 NLM
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|a Cyclohexenes
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|a bromotyrosine
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|a Tyrosine
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|a 42HK56048U
|2 NLM
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|a Davis, Rohan A
|e verfasserin
|4 aut
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|a Quinn, Ronald J
|e verfasserin
|4 aut
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|i Enthalten in
|t Magnetic resonance in chemistry : MRC
|d 1985
|g 50(2012), 11 vom: 04. Nov., Seite 749-54
|w (DE-627)NLM098179667
|x 1097-458X
|7 nnns
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| 773 |
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|g volume:50
|g year:2012
|g number:11
|g day:04
|g month:11
|g pages:749-54
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|u http://dx.doi.org/10.1002/mrc.3868
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