Chiral-Selective Aminoacylation of an RNA Minihelix

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Science  27 Aug 2004:
Vol. 305, Issue 5688, pp. 1253
DOI: 10.1126/science.1099141

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Amino acids in natural proteins have a chiral, asymmetric center at the α carbon that is of the L-configuration. The sugar backbone of natural RNAs are also homochiral, but of the D-configuration. Because protein synthesis requires the aminoacylation of RNA, it is this step that could have provided chiral selectivity. Here we show that an RNA minihelix was aminoacylated by an aminoacyl-phosphate-D-oligonucleotide with a clear preference for L- as opposed to D-amino acids. A mirror-image RNA system showed the opposite selectivity. These results suggest the possibility that the selection of L-amino acids for proteins was determined by the stereochemistry of RNA.

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