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Science 18 September 1981:
Vol. 213. no. 4514, pp. 1379 - 1381
DOI: 10.1126/science.7268441
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Articles

Science, Vol 213, Issue 4514, 1379-1381
Copyright © 1981 by American Association for the Advancement of Science

articles

Chiral recognition by nucleosides and nucleotides: resolution of helicenes by high-performance liquid chromatography

YH Kim, A Tishbee, and E Gil-Av

Chiral recognition by nucleosides and nucleotides coated on silica gel was studied by high-performance liquid chromatography. Helicenes, which are chiral polyaromatic hydrocarbons, were used as probes. Stereoselectivity was detected when the nucleobase was a purine (adenosine 3', 5'-monophosphate, an guanosine), but was not detected with the pyrimidine derivative uridine. For a given nucleobase (adenine), all changes in the ribose moiety affected the resolution factors, which ranged between 1.03 and 1.074. These results might be relevant to the enantioselectivity of carcinogenic metabolites of polyaromatic hydrocarbons.




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Science. ISSN 0036-8075 (print), 1095-9203 (online)