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Advances in space research : the official journal of the Committee on Space Research (COSPAR)

On the stereoselective aminoacylation of RNA.


PMID 11537770

Abstract

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.