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      https://www.ias.ac.in/article/fulltext/jcsc/127/09/1563-1569

    • Keywords

       

      Bicyclic tetrapeptides; ring-closing metathesis; aliphatic loop length; HDAC inhibitors.

    • Abstract

       

      Cyclic peptides show diverse biological activities and are considered as good therapeutic agents due to structural rigidity, receptor selectivity and biochemical stability. We have developed bicyclic tetrapeptide HDAC inhibitors based on different cyclic tetrapeptide scaffolds. For the synthesis of these bicyclic tetrapeptides, two cyclization steps, namely, peptide cyclization and fusion of aliphatic side chains by ring closing metathesis (RCM) were involved. In the course of these syntheses, we have established two facts: a lower limit of aliphatic loop length and better synthetic route for bicyclic tetrapeptide synthesis. It was found that nine methylene loop length is the lower limit for aliphatic loop and the synthetic route selection depended on the configuration of amino acids in the cyclic tetrapeptide scaffold. RCM followed by peptide cyclization was the proper route for LDLD configuration and the reverse route was suitable for LLLD configuration.

    • Author Affiliations

       

      Md Nurul Islam1 2 Md Shahidul Islam1 2 Md Ashraful Hoque1 3 Tamaki Kato1 Norikazu Nishino1

      1. Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan
      2. Department of Chemistry, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh
      3. Department of Biochemistry and Molecular Biology, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh
    • Dates

       
  • Journal of Chemical Sciences | News

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