227798-11-0Relevant academic research and scientific papers
Peptide nucleic acids and their phosphonate analogues: II 1. Synthesis and physicochemical properties of hybrids containing serine and 4-hydroxyproline residues
Efimov,Buryakova,Choob,Chakhmakhcheva
, p. 545 - 555 (2007/10/03)
DNA mimics representing hybrids of peptide nucleic acids (PNA) or PNA phosphonate analogues (pPNA) with hydroxyamino acid derivatives, L-serine and L-4-trans-hydroxyproline, were synthesized. Preparative synthesis of monomers and some heterodimers derived from serine and hydroxyproline was developed. The corresponding mimic oligomers including pyrene-containing derivatives were prepared by the solid-phase automated synthesis. Ability of the resulting NA analogues to hybridize specifically to the DNA and RNA complementary strands was studied. It was shown that homothymine hybrids containing PNA or pPNA monomers alternating with hydroxyproline-derived monomers can form stable complexes with the complementary oligonucleotides, whose melting temperatures are close to those of equivalent PNA complexes.
Optimization of the binding properties of PNA-(5')-DNA chimerae
Van Der Laan,Havenaar,Oosting,Kuyl-Yeheskiely,Uhlmann,Van Boom
, p. 663 - 668 (2007/10/03)
The synthesis and evaluation of PNA-(5')-DNA chimerae containing either a 5'-amide (i.e. 1a), a 5'-phosphodiester (i.e. 1b) or 5'-phosphonate linkages (i.e. 1c,d) at the junction site are described. The 5'-linkages could be installed using either 5'-amino-5'-deoxythymidine phosphoramidite 2, O-[2-(2-aminoethyl)-(thymin-1-ylacetyl)amino]ethyl phosphoramidite 3, N-(2-aminoethyl)-N-(thymin-1-ylacetyl)aminomethyl phosphonate 4 or N-(2-aminoethyl)-N-(allyloxycarbonyl)aminomethyl phosphonate 5 as building blocks, respectively. It is shown that PNA-(5')-DNA of type 1a-c have a higher binding affinity with complementary RNA than native DNA, and that the antisense activity is mainly due to RNase H.
Peptide nucleic acids and their phosphonate analogues: Synthesis and hybridization properties
Efimov,Buryakova,Choob,Chakhmakhcheva
, p. 618 - 630 (2007/10/03)
The synthesis of a series of DNA mimics-peptide nucleic acids, phosphonate analogues of peptide nucleic acids, and their hybrids - is described. The preparative synthesis of the corresponding monomers and the solid phase automated synthesis of oligomers-mimics are developed. Modified phosphonate analogues of peptide nucleic acids, in particular, chiral derivatives and those with additional hydroxyl groups in the side chains of the backbone, as well as pyrene derivatives of peptide nucleic acids and their phosphonate analogues, are prepared. The affinity of the resulting oligomers specifically to hybridize to DNA and RNA complementary chains is studied. It is shown that phosphonate analogues of peptide nucleic acids and their hybrids with peptide nucleic acids can form complexes with the DNA and RNA complementary strands, the stability of the complexes increasing in parallel with the increase in the number of peptide nucleic acid residues in the chain of the mimic. This property, along with good water solubility, provides the precondition for further evaluation of these compounds as antisense and antigene agents.
