Peptide Nucleic Acids with a Conformationally Constrained Chiral Cyclohexyl-Derived Backbone

✍ Scribed by Pierre Lagriffoule; Magdalena Eriksson; Kristine Kilså Jensen; Peter E. Nielsen; Pernilla Wittung; Bengt Nordén; Ole Buchardt

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 840 KB
• Volume: 3
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.19970030613

✦ Synopsis

Peptide nucleic acid (PNA) is an achiral nucleic acid mimic with a backbone consisting of partly flexible aminoethyl glycine units. By replacing the aminoethyl portion of the backbone by an amino cyclohexyl moiety. either in the ( S , S ) or the (R,R) configuration, we havc synthesized conformationally constrained PNA residues. PNA oligomers containing (S,S)-cyclohexyl residues were able to form hybrid complexes with DNA or RNA, with little effect on the thermal stability (AT,, = * I "C per (S,S) unit, depending on their number and the sequence). I n contrast. incorporation of the (R,R) isomer resulted in a drastic decrease in the stability of the PNA-DNA (or