• A facile route to synthesize N-(Boc-Aminoethylglycin)thymine Ethyl Ester, application to the synthesis of PNA-oligonucleotide conjugates

    • Fulltext

       

        Click here to view fulltext PDF


      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/132/0032

    • Keywords

       

      Ethylenediamine; peptide nucleic acid synthesis; nucleic acid analogs; nucleobase.

    • Abstract

       

      Peptide nucleic acid oligonucleotide conjugates are attracting immense interest currently because of their use in the biomedical and diagnostic field as antigene and molecular sensors. The efficient PNA synthesis methods can reduce their cost and may increase availability for their wider use. Here we described afacile synthesis of the peptide nucleic acid monomer N-(Boc-Aminoethylglycin)thymine Ethyl Ester [Ethyl2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido) acetate]. The monomer N-(Boc-Aeg)thymine Ethyl Ester has been prepared in a good yield (96%) by highly efficient procedure involving direct coupling of nucleobase thymine with the backbone Ethyl N-(Bocaminoethyl)-N-(chloroacetyl)glycinate, which was prepared from the reaction of Ethyl N-[(2-Boc-amino)-ethyl]glycinate with chlroacetylchloride. The key intermediate Ethyl N-[(2-Boc-amino)-ethyl]glycinate involved in the synthesis has been prepared via a scalable and cost-effective route with a yield of (98%). The thyminyl PNA monomer was reported to be used in various synthetic applications, and our cost-effective, highly scalable method of synthesis will expand its wider use.

    • Author Affiliations

       

      ANURADHA DAS1 BISWARANJAN PRADHAN2

      1. National Institute of Science Education and Research Bhubaneswar (HBNI), PO: Bhimpur-Padanpur, Jatni, Odisha 752050, India
      2. S. K. Dash Center of Excellence of Biosciences and Engineering and Technology, Indian Institute of Technology Bhubaneswar, Arugul, Jatni, Odisha 752050, India
    • Dates

       
  • Journal of Chemical Sciences | News

    • Editorial Note on Continuous Article Publication

      Posted on July 25, 2019

      Click here for Editorial Note on CAP Mode

© 2021-2022 Indian Academy of Sciences, Bengaluru.