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Sequence‐Specific DNA Alkylation by Tandem Py–Im Polyamide Conjugates
Author(s) -
Taylor Rhys Dylan,
Kawamoto Yusuke,
Hashiya Kaori,
Bando Toshikazu,
Sugiyama Hiroshi
Publication year - 2014
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201402331
Subject(s) - polyamide , moiety , alkylation , chemistry , dna , linker , tandem , sequence (biology) , conjugate , combinatorial chemistry , biochemistry , stereochemistry , organic chemistry , materials science , mathematical analysis , mathematics , computer science , composite material , operating system , catalysis
Tandem N ‐methylpyrrole N ‐methylimidazole (PyIm) polyamides with good sequence‐specific DNA‐alkylating activities have been designed and synthesized. Three alkylating tandem PyIm polyamides with different linkers, which each contained the same moiety for the recognition of a 10 bp DNA sequence, were evaluated for their reactivity and selectivity by DNA alkylation, using high‐resolution denaturing gel electrophoresis. All three conjugates displayed high reactivities for the target sequence. In particular, polyamide 1 , which contained a β‐alanine linker, displayed the most‐selective sequence‐specific alkylation towards the target 10 bp DNA sequence. The tandem PyIm polyamide conjugates displayed greater sequence‐specific DNA alkylation than conventional hairpin PyIm polyamide conjugates ( 4 and 5 ). For further research, the design of tandem PyIm polyamide conjugates could play an important role in targeting specific gene sequences.