The utility of unnatural fluorescent amino acids (FUAAs) as imaging agents to investigate intracellular processes and biological structure and function is indispensible. We have designed and synthesized FUAAs derived from natural amino acid, L-tyrosine. Up on changing the structure and electronics, these compounds showed a broader emission range including NIR emission. More importantly, these compounds exhibited pH and redox sensitivities. Later, we incorporated these amino acids in to a cell penetrating peptide sequence by standard solid phase peptide synthesis (SSPS) and internalization of the resultant peptides was visualized using confocal microscopy, showing the potential of these FUAAs in peptide synthesis and site-specific labeling of the peptides.

Tyrosine-derived oligo meta-phenylenevinylenes (OMPVs): Enantiomerically pure stimuli-responsive fluorescent amino acids

247th National Meeting (2014)

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