Thin layer chromatography and principal component analysis for the study of the interaction of amino acids with some antisense nucleosides

The interaction of 23 antisense nucleosides with amino acids was studied by charge-transfer reversed-phase thin-layer chromatography and the retention matrix was evaluated by principal component analysis. The majority of amino acids had a negligible effect on the retention of nucleosides. Only amino acids with bulky ring structures (Trp and Phe) significantly decreased the retention of nucleosides. This phenomenon indicates the outstanding role of stacking interactions between the ring structures of antisense nucleosides and Trp and Phe. The length of the alkyl substituent at the 5 position markedly influenced the strength of interaction whereas the branching of the chain or the presence of double or triple bonds had a very low impact on the interaction.