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Chiral-selective aminoacylation of an RNA minihelix: Mechanistic features and chiral suppression

Tamura, Koji ; Schimmel, Paul R

Proceedings of the National Academy of Sciences of the United States of America, 12 September 2006, Vol.103(37), pp.13750-2 [Rivista Peer Reviewed]

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  • Titolo:
    Chiral-selective aminoacylation of an RNA minihelix: Mechanistic features and chiral suppression
  • Autore: Tamura, Koji ; Schimmel, Paul R
  • Descrizione: Aminoacylation of RNA minihelices is speculated to be a key step in the transition from the putative RNA world to the theater of proteins. This reaction affords the opportunity to make chiral selection of an l- or d-amino acid and thus determine the ultimate chirality that is incorporated into proteins. Previous work showed chiral preference of aminoacylation with a nonprotein, nonribozyme, RNA-directed aminoacylation system. This preference was, in turn, determined by the preexisting chirality of the RNA. The alpha-amino group attached to the asymmetric alpha-carbon of the amino acid was an obvious candidate to play a role in chiral selectivity through interactions with the RNA. Also not clear was whether a simple manipulation could change the chiral selectivity, thereby giving insight into the basis of chiral selection in the first place. Here we show, surprisingly, no role for the free alpha-amino group in chiral selection. However, by a sequence manipulation, chiral preference was suppressed and partly reversed. This result and those with further RNA constructs support the idea that the chiral preference for an l-amino acid in these constructs depends on avoiding a sugar-pucker-sensitive steric clash between a pendant group of a base with the amino acid side chain.
  • Fa parte di: Proceedings of the National Academy of Sciences of the United States of America, 12 September 2006, Vol.103(37), pp.13750-2
  • Soggetti: Transfer RNA Aminoacylation ; Amino Acids -- Chemistry ; RNA -- Chemistry
  • Lingua: Inglese
  • Identificativo: ISSN: 0027-8424 ; PMID: 16950872 Version:1
  • Fonte: MEDLINE/PubMed (U.S. National Library of Medicine)

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