A cyclopentane conformational restraint for a peptide nucleic acid: design, asymmetric synthesis, and improved binding affinity to DNA and RNA.
[structure: see text] A strategy to restrict the highly flexible backbone conformation of a peptide nucleic acid (PNA) by incorporation of a cyclopentane ring is proposed. An asymmetric synthesis of cyclopentane-modified PNA is reported, and its binding properties were determined. The cyclopentane ring leads to a significant improvement in the binding properties of the resulting PNA to DNA and RNA.
Myers
Michael C
MC
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Witschi
Mark A
MA
Larionova
Nataliya V
NV
Franck
John M
JM
Haynes
Russell D
RD
Hara
Toshiaki
T
Grajkowski
Andrzej
A
Appella
Daniel H
DH
D000478:Alkylation; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000378:metabolism*; D004247:DNA / Q000378:metabolism*; D015195:Drug Design; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000378:metabolism*; D012313:RNA / Q000378:metabolism*; D013237:Stereoisomerism
D003517:Cyclopentanes; D020135:Peptide Nucleic Acids; D012313:RNA; D004247:DNA