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Chiral Peptide Nucleic Acids (PNAs): Helix Handedness and DNA Recognition

✍ Scribed by Stefano Sforza; Gerald Haaima; Rosangela Marchelli; Peter E. Nielsen


Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
211 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis


Peptide Nucleic Acids (PNAs) are DNA mimics in which the chiral monomer inserted in the middle of the strand is able to induce a strong preference in the helix handedness of a deoxyribose phosphate backbone has been replaced by a pseudo-peptide skeleton composed of N-(2-aminoethyl)-PNA-PNA duplex. The effect is increased by the presence of three chiral charged monomers. The L-Lys-and L-Asp-PNAs glycine units; they bind to complementary DNA strands with high affinity and selectivity. In order to study the effect of induced a preference for the left-handed and the D-Lys and D-Glu-PNAs for the right-handed conformation. As expected, stereogenic centers within the backbone on PNA preorganization and DNA binding properties, chiral PNA the PNA-DNA duplexes are dominated by the DNA strand and thus are right-handed with both D-and L-PNAs. decamers were synthesized which contained thymine monomers derived from L-Leu and D-or L-Lys inserted either However, the D-PNAs, being inherently right-handed, lead to more stable PNA-DNA duplexes than the L-PNAs. The at C-terminus and/or in the middle of an achiral PNA strand. PNAs containing three chiral thymine monomers derived lysine-based PNAs form more stable complexes with the DNA at low ionic strength, due to the electrostatic from L-Leu, D-or L-Lys, L-Asp, or D-Glu were also synthesized. CD spectral analyses showed that a charged interactions between the charged lysine side chain and DNA.

DNA, [8] and especially a PNA-PNA duplex [9] and a PNA 2 -


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