engleski

Synthesis of photo-activable oligopeptides for targeting biomolecules

Peptides were not commonly encountered as drugs because of difficulty to penetrate through cell membranes and proteolysis by intracellular enzymes. However, these problems have been circumvented by structural modifications, and particularly incorporation of unnatural amino acids. Nowadays, peptides are more frequently considered as drugs candidates since they form non-covalent complexes with proteins and DNA, which in principle enables selective targeting of a desired enzyme or a gene sequence. Herein we will present synthesis of different dipeptides and tripetides that contain modified tyrosine, as shown in one example by structure 1. Photochemical reaction of deamination in these peptides deliver quinone methide (QM) derivatives. In past 20 years, QMs have been intensively investigated reactive intermediates because of their biological activity. It has been demonstrated that QMs react with DNA and proteins. Photochemical reaction of deamination provides a mild and easy access to QMs, especially applicable in biological systems since photoexcitation allows for temporal and spatial control of the process.

unnatural amino acids; oligopeptides; biomolecules

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