Chiral Peptide Nucleic Acids (PNAs): Helix Handedness and DNA Recognition
β 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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β¦ 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of the strand is able to induce a strong preference in the helix handedness of a deoxyribose phosphate backbone has been replaced by a pseudo-peptide skeleton composed of N-(2-aminoethyl)-PNA-PNA duplex.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 -
π SIMILAR VOLUMES
Peptide nucleic acids are DNA mimics able to form duplexes with complementary DNA or RNA strands of remarkable affinity and selectivity. Oligopyrimidine PNA can displace one strand of dsDNA by forming PNA(2):DNA triplexes of very high stability. Many PNA analogs have been described in recent years,
Polyamide or peptide nucleic acids (PNAs), first described in 1991, [1] are DNA analogues based entirely on an achiral polyamide backbone (Scheme 1). The PNAs undergo sequence-specific and efficient Watson Β± Crick base pairing with Scheme 1. Sections of the chemical structures of deoxyribonucleic ac
Synthesis of a Monocharged Peptide Nucleic Acid (PNA) Analogue and Its Recognition as Substrate by DNA Polymerases. -The preparation of a novel phosphoramidite monomer based on thyminyl acetic acid coupled to a secondary nitrogen of 2-(2-amino-ethylamino)ethanol (III) is described. This monomer can