engleski

SYNTHESIS OF PYRROLOCYTOSINE-GUANIDINIOCARBONYL PYRROLE CATIONS AS A NEW TYPE OF MOLECULAR PROBES

Hybrid compounds which combine several different binding modes (intercalation, groove binding and electrostatic interactions) can distinguish various ds-DNA/RNAs based on very small differences in their secondary structures. We designed and synthesized new type of molecular probes combining two fragments which are well known to interact with nucleic acids: fluorescent pyrrolocytosine nucleobase and guanidiniocarbonyl pyrrole cation known as a highly efficient DNA minor groove binder. Novel fluorescent analogue of cytosine 2 was synthesized from N4-benzoyl-5-iodocytosine derivative 1 by a one pot sequential Sonogashira cross-coupling and annulation with propargylglycine. Amino acid monomer 2 was then coupled to the dipeptide Gly-Lys giving compound 3, which is attached to guanidinocarbonyl pyrrole carboxylic acid, resulting in hybrid multipurpose probes 4 and 5, and which may have potential as in vivo sensors.

pyrrolocytosine ; guanidiniocarbonyl pyrrole cation

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