Abstract
‘Head-to-head’ oligo- N-methylpyrrole peptide dimers linked by a methano[1,5]diazocin scaffold are presented in racemic as well as chiral fashion. Their DNA binding activities were assayed on calf thymus DNA, poly(dA-dT) 2, and poly(dC-dG) 2 by NMR and ECD spectroscopies, and fluorescence probe displacement assay. The presented dimers prefer AT sequences, but show higher affinity to poly(dC-dG) 2 than distamycin A. The (4 R,9 R) configuration of methanodiazocin bridge was found to be better suited for interaction with ct-DNA and poly(dA-dT) 2 than (4 S,9 S) configuration.
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