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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

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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 at the 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.

Graphical Abstract

Base catalyzed cyclization of 2-(2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile and subsequent oxidative substitution by free amine group leads to the formation of a chromophore, which permits naked-eye detection of the deprotected peptide on resin support.

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Acknowledgements

We thank Ms. I Janani for help in octapeptide binding to A431 cells. This work was carried out as part of the PhD program registered at the University of Madras, using a grant BSC0201 from Council of Scientific and Industrial Research, New Delhi.

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Authors and Affiliations

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

    K Rajavenkatesh, S Santoshkumar, K Purnasai & S Thennarasu

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  1. K Rajavenkatesh
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  2. S Santoshkumar
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  3. K Purnasai
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  4. S Thennarasu
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Correspondence to S Thennarasu.

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Rajavenkatesh, K., Santoshkumar, S., Purnasai, K. et al. A facile method for monitoring solid-phase peptide synthesis and for N-terminal modification of peptides: synthesis of short peptides for imaging specific cells. J Chem Sci 131, 108 (2019). https://doi.org/10.1007/s12039-019-1683-9

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  • DOI: https://doi.org/10.1007/s12039-019-1683-9

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