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Synthesis of DNA‐Sequence‐Selective Hairpin Polyamide Platinum Complexes
Author(s) -
Taleb Robin I.,
Jaramillo David,
Wheate Nial J.,
AldrichWright Janice R.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601486
Subject(s) - platinum , imidazole , pyrrole , dna , chemistry , polyamide , combinatorial chemistry , nuclear magnetic resonance spectroscopy , molecule , sequence (biology) , yield (engineering) , stereochemistry , polymer chemistry , materials science , organic chemistry , biochemistry , metallurgy , catalysis
Two DNA‐sequence‐selective hairpin polyamide platinum(II) complexes, containing pyrrole and imidazole heterocyclic rings, have been synthesised by different methods. A six‐ring complex, selective for (A/T)GGG(A/T) DNA sequences, was made by using solid‐phase synthesis, whilst an eight‐ring complex, selective for (A/T)CCTG(A/T) DNA sequences, was made by utilising standard wet chemistry. Solid‐phase synthesis resulted in a significantly higher yield, required less purification and is more efficient than the wet synthesis; as such, it is the preferred method for further work. The metal complexes were characterised by 1 H and 195 Pt NMR spectroscopy and ESI mass spectrometry. The two compounds provide a foundation for the synthesis of more complex molecules containing multiple hairpins and/or platinum groups.