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Journal of Molecular Evolution

, Volume 31, Issue 4, pp 251–256 | Cite as

Chemical esterification of 5′-AMP occurs predominantly at the 2′ position

  • James C. LaceyJr.
  • Ralph D. Thomas
  • Nalinie SMD Wickaramasinghe
  • Charles L. Watkins
Article

Summary

We describe experiments here which show that chemical esterification of 5′-adenylic acid (5′-AMP) withN-acetylD-orL-phenylalanine (Ac-D- or Ac-L-Phe) imidazolide occurs principally, if not exclusively, at the 2′ position. Furthermore, in experiments with the formation of the 2′–3′ diester with butyric acid andN-acetyl glycine (Ac-Gly), we found the second esterification was also predominantly at the 2′ position. This means that mixed diesters can be predictably prepared with the positions of the substituents known. The results are consistent with a model for the preferential catalytic synthesis ofL-based peptides via a 2′–3′ diester intermediate of purine monoribonucleotides.

Key words

5′-AMP aminoacylation Site of esterification Origin of protein synthesis 

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Copyright information

© Springer-Verlag New York Inc. 1990

Authors and Affiliations

  • James C. LaceyJr.
    • 1
  • Ralph D. Thomas
    • 1
  • Nalinie SMD Wickaramasinghe
    • 1
  • Charles L. Watkins
    • 2
  1. 1.Department of BiochemistryUniversity of Alabama at BirminghamBirminghamUSA
  2. 2.Department of ChemistryUniversity of Alabama at BirminghamBirminghamUSA

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