ArticleExperientia1992
Preferential hydrophobic interactions are responsible for a preference of D-amino acids in the aminoacylation of 5'-AMP with hydrophobic amino acids.
Article in Experientia, 1992. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Article
- Couplings of character and of chirality in the origin of the genetic system.Journal of molecular evolution · 1993Article
- Alterations in interleukin-6 production by LPS- and Con A-stimulated mixed splenocytes, spleen macrophages and lymphocytes in prenatally diazepam-exposed rats.Agents and actions · 1993Article
- Mixed anhydrides (phosphoric-carboxyl) are also formed in the esterification of 5'-AMP with N-acetylaminoacyl imidazolides: implications regarding the origin of protein synthesis.Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life · 1992Article
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Authors and funding
3 authors.
Funding
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Abstract
We have studied the chemistry of aminoacyl AMP to model reactions at the 3' terminus of aminoacyl tRNA for the purpose of understanding the origin of protein synthesis. The present studies relate to the D, L preference in the esterification of 5'-AMP. All N-acetyl amino acids we studied showed faster reaction of the D-isomer, with a generally decreasing preference for D-isomer as the hydrophobicity of the amino acid decreased. The beta-branched amino acids, Ile and Val, showed an extreme preference for D-isomer. Ac-Leu, the gamma-branched amino acid, showed a slightly low D/L ratio relative to its hydrophobicity. The molecular basis for these preferences for D-isomer is understandable in the light of our previous studies and seems to be due to preferential hydrophobic interaction of the D-isomer with adenine. The preference for hydrophobic D-amino acids can be decreased by addition of an organic solvent to the reaction medium. Conversely, peptidylation with Ac-PhePhe shows a preference for the LL isomer over the DD isomer.
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