On the stereoselective aminoacylation of RNA

Aminoacylation of the “internal” 2′-hydroxyl groups of poly(A) with the imidazolide of racemic DL-leucine resulted in the formation of an enantiomeric excess of the D-ester, whereas aminoacylation with the imidazolide of racemic N-3,5-dinitrobenzoyl-DL-leucine gave an enantiomeric excess of the L-ester. Comparison of these results with those obtained earlier for alanine shows that the larger side chain tends to favor the formation of the D-ester. High resolution proton magnetic resonance spectroscopy was performed on the D- and L-alanyl “internal” 2′-esters of 3′,5′-ApA. The resonance of the side chain methyl group of the D-ester is upfield from that of the L-ester, and the separation of the peaks increases with a decrease in temperature.