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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Feb 6

PMID 36743074

Authors

Camelia Kitoun

Saidbakhrom Saidjalolov

Delphine Bouquet

Fabiola Djago

Quentin Blancart Remaury

Bruno Sargueil

Pauline Poinot

Melanie Etheve-Quelquejeu

Laura Iannazzo

Affiliations

Soon will be listed here.

Abstract

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 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.

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PMID: 39835399 PMC: 11747965. DOI: 10.1039/d4tb01897d.

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