2019
DOI: 10.1007/s12039-019-1683-9
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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

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 all… Show more

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Cited by 2 publications
(1 citation statement)
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“…A naked-eye detection of the free amino group has been tested by Rajavenkatesh et al [37] using solidphase peptide synthesis. It is a catalytic cyclisation technique of 2-(2-oxo-2H-acenaphthylene-1-ylidene)malononitrile and oxidative substitution of aryl moiety by free amine group existing in N-terminal position of the peptide chain.…”
Section: Synthesis Of Peptide and Proteinsmentioning
confidence: 99%
“…A naked-eye detection of the free amino group has been tested by Rajavenkatesh et al [37] using solidphase peptide synthesis. It is a catalytic cyclisation technique of 2-(2-oxo-2H-acenaphthylene-1-ylidene)malononitrile and oxidative substitution of aryl moiety by free amine group existing in N-terminal position of the peptide chain.…”
Section: Synthesis Of Peptide and Proteinsmentioning
confidence: 99%