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Olefinic Peptide Nucleic Acids (OPAs): New Aspects of the Molecular Recognition of DNA by PNA
Author(s) -
Schütz Rolf,
Cantin Michel,
Roberts Christopher,
Greiner Beate,
Uhlmann Eugen,
Leumann Christian
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000403)39:7<1250::aid-anie1250>3.0.co;2-e
Subject(s) - nucleic acid , dna , peptide nucleic acid , linker , chemistry , peptide , isostructural , amide , combinatorial chemistry , nucleic acid analogue , base pair , stereochemistry , nucleic acid thermodynamics , biochemistry , crystallography , base sequence , computer science , crystal structure , operating system
Vive la différence ! Replacement of the base‐linker amide functionality in peptide nucleic acids (PNAs) by an isostructural C−C double bond (shown schematically) leads to a dramatic change in DNA affinity, preferred strand orientation, and triplex‐forming properties, and thus highlights the importance of electrostatic properties over geometric properties of the amide functionality in PNA/DNA recognition.