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Novel DNA Analogues...
Novel DNA Analogues with 2-, 3- and 4-Pyridylphosphonate Internucleotide Bonds : Synthesis and Hybridisation Properties
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- Zmudzka, Katarzyna (author)
- Polish Acad Sci, Ctr Mol & Macromol Studies
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- Johansson, Tommy (author)
- Stockholms universitet,Institutionen för organisk kemi
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- Wojcik, Marzena (author)
- Polish Acad Sci, Ctr Mol & Macromol Studies
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- Janicka, Magdalena (author)
- Polish Acad Sci, Ctr Mol & Macromol Studies
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- Nowak, Marian (author)
- Polish Acad Sci, Ctr Mol & Macromol Studies
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Stawinski, Jacek (author)
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- Nawrot, Barbara (author)
- Polish Acad Sci, Ctr Mol & Macromol Studies
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(creator_code:org_t)
- Royal Society of Chemistry, 2003
- 2003
- English.
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In: New Journal of Chemistry. - : Royal Society of Chemistry. - 1144-0546 .- 1369-9261. ; 27:12, s. 1698-1705
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Oligothymidylates modified with stereodefined 2-pyridyl-, 3-pyridyl- and 4-pyridylphosphonate moieties at one or two juxtaposed internucleotide positions were prepared, and their avidity towards complementary single stranded DNA and RNA, as well as toward double stranded DNA were evaluated by UV melting temperature and CD studies. It was found that the sense of chirality at the phosphorus centre and the position of the nitrogen atom in the pyridyl ring of a pyridylphosphonate moiety are important factors governing stability of double- and triple-stranded complexes formed by these oligonucleotides. DNA/DNA and DNA/RNA duplexes containing oligothymidylate strands with R-P-pyridylphosphonate units differed only slightly from unmodified reference complexes. In contrast to this, the S-P-pyridylphosphonate derivatives exhibited lower binding affinity than both their R-P-counterparts and the unmodified reference oligonucleotide T-20. Triplexes of oligo(thymidyl pyridylphosphonate)s with hairpin oligomer d(A(21)C(4)T(21)) were found mostly to be thermodynamically slightly more stable in pH 7.4 and less stable in pH 5.0 than non-modified complexes. As expected, oligonucleotides with pyridylphosphonate internucleotide bonds were recognised by 3'- and 5'-exonucleases but the chimeric oligonucleotide chains were not cleaved at the modi. cation sites.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Keyword
- IONIC OLIGONUCLEOSIDE METHYLPHOSPHONATES; MOLECULAR-DYNAMICS SIMULATION; HUMAN-IMMUNODEFICIENCY-VIRUS; H-PHOSPHONOTHIOATE DIESTERS; ANTISENSE OLIGONUCLEOTIDES; STEREOSPECIFIC OXIDATION; PHOSPHATE BACKBONE; MINOR-GROOVE; HUMAN PLASMA; B-DNA
- Organic chemistry
- Organisk kemi
- organisk kemi
- Organic Chemistry
Publication and Content Type
- ref (subject category)
- art (subject category)
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