Linked Life Data

3558546

Source:http://linkedlifedata.com/resource/pubmed/id/3558546

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PredicateObject
rdf:type
lifeskim:mentions
pubmed:dateCreated
1987-4-27
pubmed:abstractText
The direct resolution of K-region cis- and trans-dihydrodiol enantiomers of 14 unsubstituted and methyl- and bromo-substituted benz[a]anthracene (BA) derivatives was investigated by high-performance liquid chromatography with commercially available columns, packed with gamma-aminopropylsilanized silica to which either (R)-N-(3,5-dinitrobenzoyl)phenylglycine (R-DNBPG) or (S)-N-(3,5-dinitrobenzoyl)leucine (S-DNBL) is either ionically or covalently bonded. BA derivatives used in this study include: BA, 1-methyl-BA, 4-methyl-BA, 7-methyl-BA, 8-methyl-BA, 10-methyl-BA, 11-methyl-BA, 12-methyl-BA, 7,12-dimethyl-BA, 7-bromo-BA, 7-bromo-1-methyl-BA, 7-bromo-11-methyl-BA, 7-bromo-12-methyl-BA, and 3-methylcholanthrene. The enantiomers of BA trans-5,6-dihydrodiol were the only compounds not resolved by any of the four chiral stationary phases (CSPs) tested. The results indicate that conformational preference of the hydroxyl group is one of the most important factor in determining the elution order of dihydrodiol enantiomers. The presence and the location of a substituent and the molecular size and shape of the dihydrodiols can significantly affect the efficiency of enantiomeric resolution. In general, the ionically bonded R-DNBPG provides the best resolution of enantiomeric quasidiequatorial trans-dihydrodiols and the R,R enantiomers are consistently more strongly retained. In contrast, the enantiomeric pairs of quasidiaxial trans-dihydrodiols are generally better resolved by the covalently bonded R-DNBPG, and the S,S enantiomers are more strongly retained. The enantiomers of cis-dihydrodiols having hydroxyl groups that adopt quasiequatorial-quasiaxial and/or quasiaxial-quasiequatorial conformations are more consistently resolved by the ionically bonded S-DNBL and in all cases the S,R enantiomers are more strongly retained. Thus, it is possible to choose a CSP which resolves the K-region dihydrodiol enantiomers with a predictable elution order.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Dec
pubmed:issn
0021-9673
pubmed:author
pubmed:issnType
Print
pubmed:day
26
pubmed:volume
371
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
195-209
pubmed:dateRevised
2008-11-21
pubmed:meshHeading
pubmed:year
1986
pubmed:articleTitle
Elution order-absolute configuration relationship of K-region dihydrodiol enantiomers of benz[a]anthracene derivatives in chiral stationary phase high-performance liquid chromatography.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S.