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A Nucleobase‐Discriminating Pyrrolo‐dC Click Adduct Designed for DNA Fluorescence Mismatch Sensing
Author(s) -
Ming Xin,
Seela Frank
Publication year - 2012
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.201103385
Subject(s) - nucleobase , oligonucleotide , linker , moiety , adduct , click chemistry , dna , chemistry , triazole , combinatorial chemistry , fluorescence , stereochemistry , biochemistry , organic chemistry , computer science , physics , quantum mechanics , operating system
New pyrrolo‐dC click adducts ( 4 and 5 ) tethered with a 1,2,3‐triazole skeleton were synthesized and oligonucleotides were prepared. The triazole system was either directly linked to the pyrrolo moiety ( 5 ) or connected via an n ‐butyl linker ( 4 ). The quantum yield of nucleoside 5 ( Φ =0.32), which is 10 times higher than those of 8‐methylpyrrolo‐dC ( 1 b , Φ =0.026) or the long linker derivative 4 ( Φ =0.03), is maintained in oligonucleotides. Compound 5 was used as a nucleobase‐discriminating fluorescence sensor in duplex DNA. Excellent mismatch discrimination was observed when 5 was positioned opposite the four canonical nucleosides. Compound 5 has the potential to be used for SNP detection in long DNA targets when conventional techniques such as high resolution melt analysis fail.