Toward encoding reactivity using double-stranded DNA. Sequence-dependent native chemical ligation of DNA binding polyamides

The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated...

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Bibliographic Details
Published in:Tetrahedron 2013-09, Vol.69 (36), p.7847-7853
Main Authors: Jiménez-Balsa, Adrian, Dodero, Verónica I., Mascareñas, José L.
Format: Article
Language:English
Subjects:
Binding
Chemical reactions
Deoxyribonucleic acid
DNA binding
Joining
Molecular recognition
Monomers
Native chemical ligation
Oligonucleotides
Polyamide resins
Polyamides
Pyrroles
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Summary:The coupling reaction between distamycin-related polyamides equipped with cysteine and thioester groups can be accelerated in the presence of double-stranded (ds) oligonucleotides with selected sequences. While the coupling reaction of reactive partners containing three pyrrole units is accelerated by dsDNAs containing ATTTTA or ATGTTA sites, the heterodimeric coupling between a tripyrrole and a polyamide equipped with two pyrroles and one imidazole, is accelerated by the latter DNA, but not by the other containing the A/T rich tract. These differences can be exploited for selecting preferred coupling pairs from a mixture of reactive monomers; therefore the reaction outcome depends on the instructions provided by the dsDNA sequence. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.05.126