(S,S)-trans-cyclopentane-constrained peptide nucleic acids. a general backbone modification that improves binding affinity and sequence specificity.
Replacing the ethylenediamine portion of aminoethylglycine peptide nucleic acids (aegPNAs) with one or more (S,S)-trans-cyclopentane diamine units significantly increases binding affinity and sequence specificity to complementary DNA, making these modified PNAs ideal for use as nucleic acid probes in genomic analysis. The synthesis and study of this new class of PNAs (tcypPNAs) is described in which trans-cyclopentane diamine has been incorporated into several positions, and in varying number, within PNA backbones of mixed-base sequences.
Pokorski
Jonathan K
JK
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Witschi
Mark A
MA
Purnell
Bethany L
BL
Appella
Daniel H
DH
D020137:Base Pair Mismatch; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity
D003517:Cyclopentanes; D020135:Peptide Nucleic Acids; D004247:DNA