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BisPNA Targeting to DNA: Effect of Neutral Loop on DNA Duplex Strand Invasion by aep PNA‐N7G/ aep PNA‐C Substituted Peptide Nucleic Acids
Author(s) -
Shirude Pravin S.,
Kumar Vaijayanti A.,
Ganesh Krish.
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200500544
Subject(s) - chemistry , linker , dna , peptide nucleic acid , duplex (building) , nucleic acid , guanine , cationic polymerization , a dna , stereochemistry , alkyl , combinatorial chemistry , biophysics , biochemistry , nucleotide , organic chemistry , gene , biology , computer science , operating system
N7‐Alkyl‐substituted guanine (N7G) as a CH + mimic has been introduced into aminoethylglycyl PNA ( aeg PNA) forming a hairpin through a neutral linker derived from bis(tetraethylene) glycol ( teg ‐ teg ). These form pH‐independent PNA 2 :DNA triplexes with complementary DNA sequences. The introduction of chiral, cationic aminoethylprolyl ( aep ) units with C and the CH + mimic N7G in the backbone of the hairpin bisPNAs with a neutral teg ‐ teg linker, influenced the recognition of complementary DNA in an orientation‐selective manner. Fluorescence assay was used to examine the process of strand invasion of the target DNA duplex by the modified hairpin bisPNAs with the neutral teg linker and comparison of results of previous studies employing cationic linkers suggested the triplex formation to be a two‐step process, with the preferred formation of HG bonds in the first step. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)