MersV1, PubMed, Corpus, bibRecord, 001496

Thermal stability and conformation of antiparallel duplexes formed by P-stereodefined phosphorothioate DNA/LNA chimeric oligomers with DNA and RNA matrices.

Identifieur interne : 001496 ( PubMed/Corpus ); précédent : 001495; suivant : 001497

Thermal stability and conformation of antiparallel duplexes formed by P-stereodefined phosphorothioate DNA/LNA chimeric oligomers with DNA and RNA matrices.

Auteurs : Katarzyna Jastrz Bska ; Anna Maciaszek ; Rafał Dolot ; Grzegorz Bujacz ; Piotr Guga

Source :

Organic & biomolecular chemistry [ 1477-0539 ] ; 2015.

RBID : pubmed:26293357

English descriptors

KwdEn :
- Base Sequence, Crystallography, X-Ray, DNA (chemistry), Models, Molecular, Nucleic Acid Conformation, Nucleic Acid Denaturation, Oligonucleotides (chemistry), Phosphorothioate Oligonucleotides (chemistry), RNA (chemistry), Stereoisomerism, Temperature.
MESH :
- chemical , chemistry : DNA, Oligonucleotides, Phosphorothioate Oligonucleotides, RNA.
- Base Sequence, Crystallography, X-Ray, Models, Molecular, Nucleic Acid Conformation, Nucleic Acid Denaturation, Stereoisomerism, Temperature.

Abstract

3'-O-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of LNA-type nucleosides (LNA-OTPs, 2a-d; B' = Thy, Ade(Bz), Cyt(Bz), Gua(dmf), respectively) were synthesized and separated into pure P-diastereomers. X-ray analysis allowed for assignment of the absolute configuration of the phosphorus atom in the detritylated, fast-eluting diastereomer 2a. The diastereomerically pure LNA-OTP monomers were used in solid phase synthesis of P-stereodefined chimeric PS-(DNA/LNA) 11-mers containing 2-3 LNA units. Formally, among the phosphorothioate oligomers the biggest enhancement in thermal stability of Watson-Crick paired duplexes was found for [SP-PS]-(DNA/LNA)/RNA duplexes (on average 8.2 °C per LNA nucleotide), followed by [RP-PS]-(DNA/LNA)/RNA (6.3 °C), [RP-PS]-(DNA/LNA)/DNA (3.8 °C) and [SP-PS]-(DNA/LNA)/DNA (2.4 °C per LNA nucleotide). However, detailed analysis of the thermal dissociation data showed that the thermal stability of (PS-LNA)-containing duplexes does not depend on the spatial orientation of the sulfur atoms. This conclusion received support from CD measurements.

DOI: 10.1039/c5ob01474c
PubMed: 26293357

Links to Exploration step

pubmed:26293357

Le document en format XML

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<author><name sortKey="Jastrz Bska, Katarzyna" sort="Jastrz Bska, Katarzyna" uniqKey="Jastrz Bska K" first="Katarzyna" last="Jastrz Bska">Katarzyna Jastrz Bska</name>
<affiliation><nlm:affiliation>Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Department of Bioorganic Chemistry, Sienkiewicza 112, 90-363 Łódź, Poland. pguga@cbmm.lodz.pl.</nlm:affiliation>
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<author><name sortKey="Maciaszek, Anna" sort="Maciaszek, Anna" uniqKey="Maciaszek A" first="Anna" last="Maciaszek">Anna Maciaszek</name>
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<author><name sortKey="Dolot, Rafal" sort="Dolot, Rafal" uniqKey="Dolot R" first="Rafał" last="Dolot">Rafał Dolot</name>
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<author><name sortKey="Bujacz, Grzegorz" sort="Bujacz, Grzegorz" uniqKey="Bujacz G" first="Grzegorz" last="Bujacz">Grzegorz Bujacz</name>
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<author><name sortKey="Guga, Piotr" sort="Guga, Piotr" uniqKey="Guga P" first="Piotr" last="Guga">Piotr Guga</name>
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<term>Oligonucleotides (chemistry)</term>
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<front><div type="abstract" xml:lang="en">3'-O-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of LNA-type nucleosides (LNA-OTPs, 2a-d; B' = Thy, Ade(Bz), Cyt(Bz), Gua(dmf), respectively) were synthesized and separated into pure P-diastereomers. X-ray analysis allowed for assignment of the absolute configuration of the phosphorus atom in the detritylated, fast-eluting diastereomer 2a. The diastereomerically pure LNA-OTP monomers were used in solid phase synthesis of P-stereodefined chimeric PS-(DNA/LNA) 11-mers containing 2-3 LNA units. Formally, among the phosphorothioate oligomers the biggest enhancement in thermal stability of Watson-Crick paired duplexes was found for [SP-PS]-(DNA/LNA)/RNA duplexes (on average 8.2 °C per LNA nucleotide), followed by [RP-PS]-(DNA/LNA)/RNA (6.3 °C), [RP-PS]-(DNA/LNA)/DNA (3.8 °C) and [SP-PS]-(DNA/LNA)/DNA (2.4 °C per LNA nucleotide). However, detailed analysis of the thermal dissociation data showed that the thermal stability of (PS-LNA)-containing duplexes does not depend on the spatial orientation of the sulfur atoms. This conclusion received support from CD measurements.</div>
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<Abstract><AbstractText>3'-O-(2-Thio-4,4-pentamethylene-1,3,2-oxathiaphospholane) derivatives of LNA-type nucleosides (LNA-OTPs, 2a-d; B' = Thy, Ade(Bz), Cyt(Bz), Gua(dmf), respectively) were synthesized and separated into pure P-diastereomers. X-ray analysis allowed for assignment of the absolute configuration of the phosphorus atom in the detritylated, fast-eluting diastereomer 2a. The diastereomerically pure LNA-OTP monomers were used in solid phase synthesis of P-stereodefined chimeric PS-(DNA/LNA) 11-mers containing 2-3 LNA units. Formally, among the phosphorothioate oligomers the biggest enhancement in thermal stability of Watson-Crick paired duplexes was found for [SP-PS]-(DNA/LNA)/RNA duplexes (on average 8.2 °C per LNA nucleotide), followed by [RP-PS]-(DNA/LNA)/RNA (6.3 °C), [RP-PS]-(DNA/LNA)/DNA (3.8 °C) and [SP-PS]-(DNA/LNA)/DNA (2.4 °C per LNA nucleotide). However, detailed analysis of the thermal dissociation data showed that the thermal stability of (PS-LNA)-containing duplexes does not depend on the spatial orientation of the sulfur atoms. This conclusion received support from CD measurements.</AbstractText>
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Thermal stability and conformation of antiparallel duplexes formed by P-stereodefined phosphorothioate DNA/LNA chimeric oligomers with DNA and RNA matrices.

Thermal stability and conformation of antiparallel duplexes formed by P-stereodefined phosphorothioate DNA/LNA chimeric oligomers with DNA and RNA matrices.

Source :

English descriptors

Abstract

Links to Exploration step

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Pour manipuler ce document sous Unix (Dilib)

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