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Article Dans Une Revue ACS Omega Année : 2023

Traceless Staudinger Ligation to Access Stable Aminoacyl- or Peptidyl-Dinucleotide

Camélia Kitoun
  • Fonction : Auteur
Saidbakhrom Saidjalolov
  • Fonction : Auteur
Delphine Bouquet
  • Fonction : Auteur
Fabiola Djago
  • Fonction : Auteur
Quentin Blancart Remaury
  • Fonction : Auteur
Pauline Poinot
Mélanie Etheve-Quelquejeu
Laura Iannazzo

Résumé

Aminoacyl-and peptidyl-tRNA are specific biomolecules involved in many biological processes, from ribosomal protein synthesis to the synthesis of peptidoglycan precursors. Here, we report a post-synthetic approach based on traceless Staudinger ligation for the synthesis of a stable amide bond to access aminoacyl-or peptidyl-di-nucleotide. A series of amino-acid and peptide ester phenyl phosphines were synthetized, and their reactivity was studied on a 2′-N 3 di-nucleotide. The corresponding 2′-amide di-nucleotides were obtained and characterized by LC-HRMS, and mechanistic interpretations of the influence of the amino acid phenyl ester phosphine were proposed. We also demonstrated that enzymatic 5′-OH phosphorylation is compatible with the acylated di-nucleotide, allowing the possibility to access stable aminoacylated-tRNA.

Domaines

Chimie
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Dates et versions

hal-04294940 , version 1 (20-11-2023)

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Camélia Kitoun, Saidbakhrom Saidjalolov, Delphine Bouquet, Fabiola Djago, Quentin Blancart Remaury, et al.. Traceless Staudinger Ligation to Access Stable Aminoacyl- or Peptidyl-Dinucleotide. ACS Omega, 2023, 8 (4), pp.3850-3860. ⟨10.1021/acsomega.2c06135⟩. ⟨hal-04294940⟩
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