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    • A facile method for monitoring solid-phase peptide synthesis and for N-terminal modification of peptides: synthesis of short peptides for imaging specific cells

      K RAJAVENKATESH S SANTOSHKUMAR K PURNASAI S THENNARASU

      Volume 131 Issue 10 October 2019 Article ID 0108

    • Fulltext

       

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/131/10/0108

    • Keywords

       

      Chemical modification of peptides; solid-phase peptide synthesis; monitoring agents; peptide labelling; cell imaging.

    • Abstract

       

      A simple method for naked-eye detection of free amine groups during solid-phase peptide synthesis is reported. The technique involves base-catalyzed cyclization of 2-(2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile (1) and subsequent oxidative substitution of aryl moiety by free amine group present atthe N-terminus of the peptide chain that leads to the formation of a chromophore, which distinguishes the deprotected peptide chain from the protected one. The reaction is fast, does not require heating, and allows N-terminal modification of peptides suitable for imaging specific cells.

    • Author Affiliations

       

      K RAJAVENKATESH S SANTOSHKUMAR K PURNASAI S THENNARASU1

      1. Organic and Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai, Tamil Nadu 600 020, India

    • Dates

       
      Published
      October 2019
      Manuscript received
      2 April 2019
      Manuscript revised
      Accepted
      22 July 2019

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