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Resolution of optical isomers by high-pressure liquid chromatography: The separation of benzo[a]pyrene trans-diol derivatives

✍ Scribed by Shen K. Yang; Harry V. Gelboin; John D. Weber; V. Sankaran; Daniel L. Fischer; James F. Engel

Publisher: Elsevier Science
Year: 1977
Tongue: English
Weight: 349 KB
Volume: 78
Category: Article
ISSN: 0003-2697
DOI: 10.1016/0003-2697(77)90112-9

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✦ Synopsis

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 corresponding enantiomers. The specific rotation, CD spectra, and ORD curves are reported. The resolution of these optical isomers permits detailed studies on the enzymatic intermediates and the mechanism of benzo[a]pyrene activation to its carcinogenic form. The method is of general usefulness for the resolution of optical isomers. 520

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