Source:http://linkedlifedata.com/resource/pubmed/id/20176363
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| Predicate | Object |
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| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
13
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| pubmed:dateCreated |
2010-3-8
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| pubmed:abstractText |
Hexahalogenated 1,1'-dimethyl-2,2'-bipyrroles (HDBPs) are a group of marine halogenated natural products (HNPs) that have been detected in environmental samples from all over the world. The most frequently described congener is the 5,5'-dichloro-1,1'-dimethyl-3,3',4,4'-tetrabromo-2,2'-bipyrrole (DBP-Br(4)Cl(2), BC-10). This compound is axially chiral, by virtue of hindered rotation about the interannular pyrrole-pyrrole bond forming stable atropisomers. This effect was proven by the separation of synthesized racemic DBP-Br(4)Cl(2) by enantioselective high performance liquid chromatography (HPLC). Pure enantiomers were isolated using enantioselective HPLC. Crystallization led to white crystals studied by X-ray analyses to determine the absolute configuration. Subsequent polarimetric measurements verified the first eluting enantiomer on HPLC as R(a)-(+)-DBP-Br(4)Cl(2) and the second as S(a)-(-)-DBP-Br(4)Cl(2). We also investigated the gas chromatography (GC) enantioseparation of DBP-Br(4)Cl(2). However, too high temperatures in the injector port led to partial racemization at temperatures >150 degrees C. GC coupled to mass spectrometry was used to study DBP-Br(4)Cl(2) in marine mammal samples. All samples contained both atropisomers of the natural product DBP-Br(4)Cl(2) with enrichment of the levo (-) enantiomer. This led to the assumption that both enantiomers of DBP-Br(4)Cl(2) were already produced in the environment.
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| pubmed:language |
eng
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| pubmed:journal | |
| pubmed:citationSubset |
IM
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| pubmed:chemical | |
| pubmed:status |
MEDLINE
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| pubmed:month |
Mar
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| pubmed:issn |
1873-3778
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| pubmed:author | |
| pubmed:copyrightInfo |
2010 Elsevier B.V. All rights reserved.
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| pubmed:issnType |
Electronic
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| pubmed:day |
26
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| pubmed:volume |
1217
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| pubmed:owner |
NLM
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| pubmed:authorsComplete |
Y
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| pubmed:pagination |
2050-5
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| pubmed:meshHeading | |
| pubmed:year |
2010
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| pubmed:articleTitle |
Enantioseparation and absolute configuration of the atropisomers of a naturally produced hexahalogenated 1,1'-dimethyl-2,2'-bipyrrole.
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| pubmed:affiliation |
Institute of Food Chemistry (170b), University of Hohenheim, Garbenstr. 28, 70599 Stuttgart, Germany.
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| pubmed:publicationType |
Journal Article
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