The optical isomers of (k)r-7,t-%dihydroxy-7&dihydrobenzo[a]pyrene and its synthetic precursor (~)r-7,r-8-dihydroxy-7,8,9,lO-tetrahydrobenzo[a]pyrene were resolved as their di-(-)menthoxyacetates using high-pressure liquid chromatography. Saponification of the resolved diesters yielded the correspon
Resolution of optical isomers by chiral high-performance liquid chromatography: Separation of dihydrodiols and tetrahydrodiols of benzo[a]pyrene and benz[a]anthracene
โ Scribed by Henri B. Weems; Shen K. Yang
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- English
- Weight
- 483 KB
- Volume
- 125
- Category
- Article
- ISSN
- 0003-2697
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โฆ Synopsis
Enantiomers of several underivatized dihydrodiols and tetrahydrodiols of benzo[a]pyrene and benz[a]anthracene have been resolved with high-performance liquid chromatography using a commercially available column packed with a o-3,5-dinitrobenzoylphenylglycine derivative of aminopropyl silica gel. Separation of optical isomers was confirmed by ultravioletvisible absorption and circular dichroism spectral analyses. This simple method has been applied to the determination of optical purity of two dihydrodiol metabolites formed from the in vitro incubation of 1 I-methylbenz[a]anthracene by rat liver microsomes.
๐ SIMILAR VOLUMES
The diastereomeric (-)-dimenthoxyacetate derivatives of (t)-tram-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene were efficiently resolved by high-pressure liquid chromatography (HPLC) on silica gel. Treatment with methanolic ammonia under mild conditions removed the menthoxyacetate groups to furnish the op