Chiral Recognition by Nucleosides and Nucleotides: Resolution of Helicenes by High-Performance Liquid Chromatography

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.