Highly efficient photochemical 2'-deoxyribonolactone formation at the diagonal loop of a 5-iodouracil-containing antiparallel G-quartet.
Identifieur interne : 000280 ( Ncbi/Checkpoint ); précédent : 000279; suivant : 000281Highly efficient photochemical 2'-deoxyribonolactone formation at the diagonal loop of a 5-iodouracil-containing antiparallel G-quartet.
Auteurs : Yan Xu [Japon] ; Hiroshi SugiyamaSource :
- Journal of the American Chemical Society [ 0002-7863 ] ; 2004.
Descripteurs français
- KwdFr :
- Chromatographie en phase liquide à haute performance, Conformation moléculaire, Indicateurs et réactifs, Lumière, Modèles moléculaires, Oligonucléotides (synthèse chimique), Oses acides (), Photochimie, Potassium (), Rayons ultraviolets, Sodium (), Thymine (), Uracile (), Uracile (analogues et dérivés).
- MESH :
- analogues et dérivés : Uracile.
- synthèse chimique : Oligonucléotides.
- Chromatographie en phase liquide à haute performance, Conformation moléculaire, Indicateurs et réactifs, Lumière, Modèles moléculaires, Oses acides, Photochimie, Potassium, Rayons ultraviolets, Sodium, Thymine, Uracile.
English descriptors
- KwdEn :
- Chromatography, High Pressure Liquid, Indicators and Reagents, Light, Models, Molecular, Molecular Conformation, Oligonucleotides (chemical synthesis), Photochemistry, Potassium (chemistry), Sodium (chemistry), Sugar Acids (chemistry), Thymine (chemistry), Ultraviolet Rays, Uracil (analogs & derivatives), Uracil (chemistry).
- MESH :
- chemical , analogs & derivatives : Uracil.
- chemical , chemical synthesis : Oligonucleotides.
- chemical , chemistry : Potassium, Sodium, Sugar Acids, Thymine, Uracil.
- chemical : Indicators and Reagents.
- Chromatography, High Pressure Liquid, Light, Models, Molecular, Molecular Conformation, Photochemistry, Ultraviolet Rays.
Abstract
To explore the structure-dependent hydrogen abstraction in antiparallel and parallel G-quartet DNA structures, the photochemical reactivity of 5-iodouracil ((I)U)-containing human telomeric DNA 22-mers was investigated under the 302 nm UV irradiation conditions. We discovered that only antiparallel ODN 4, in which the second T residue in the diagonal loop of the antiparallel G-quartet is substituted with (I)U, was rapidly consumed as compared with parallel ODN 4 and the other (I)U-containing 22-mers under the irradiation conditions. Product analysis of the photolyzate of antiparallel ODN 4 indicated that a 2'-deoxyribonolactone residue was effectively produced at the 5' side of the (I)U residue in the diagonal loop. Photochemical 2'-deoxyribonolactone formation was also found in the (I)U-containing diagonal loop of antiparallel G-quartets d(GGGGTTT(I)UGGGG)(2) and d(GGGGTT(I)UTGGGG)(2), whereas the reaction did not occur at other DNA structures, including the single-stranded form, the loop region of the hairpin, and linear four-stranded G-quartets. The results clearly indicate that this type of 2'-deoxyribonolactone formation efficiently occurrs only in the diagonal loop of the antiparallel G-quartet. Furthermore, we found that 2'-deoxyribonolactone was formed at the (I)U-containing G-rich sequence of the IgG switch regions and the 5' termini of the Rb gene, suggesting the formation of an antiparallel G-quartet with a diagonal loop in these sequences. These results suggest that the present photochemical method can be used as a specific probe for the antiparallel G-quartet with the diagonal loop.
DOI: 10.1021/ja031942h
PubMed: 15149224
Affiliations:
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sortKey="Xu, Yan" sort="Xu, Yan" uniqKey="Xu Y" first="Yan" last="Xu">Yan Xu</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Chiyoda, Tokyo 101-0062, Japan.</nlm:affiliation><country xml:lang="fr">Japon</country><wicri:regionArea>Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Chiyoda, Tokyo 101-0062</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Sugiyama, Hiroshi" sort="Sugiyama, Hiroshi" uniqKey="Sugiyama H" first="Hiroshi" last="Sugiyama">Hiroshi Sugiyama</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="ISSN">0002-7863</idno><imprint><date when="2004" type="published">2004</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Chromatography, High Pressure Liquid</term><term>Indicators and Reagents</term><term>Light</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Oligonucleotides (chemical synthesis)</term><term>Photochemistry</term><term>Potassium (chemistry)</term><term>Sodium (chemistry)</term><term>Sugar Acids (chemistry)</term><term>Thymine (chemistry)</term><term>Ultraviolet Rays</term><term>Uracil (analogs & derivatives)</term><term>Uracil (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Chromatographie en phase liquide à haute performance</term><term>Conformation moléculaire</term><term>Indicateurs et réactifs</term><term>Lumière</term><term>Modèles moléculaires</term><term>Oligonucléotides (synthèse chimique)</term><term>Oses acides ()</term><term>Photochimie</term><term>Potassium ()</term><term>Rayons ultraviolets</term><term>Sodium ()</term><term>Thymine ()</term><term>Uracile ()</term><term>Uracile (analogues et dérivés)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Uracil</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Potassium</term><term>Sodium</term><term>Sugar Acids</term><term>Thymine</term><term>Uracil</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Indicators and Reagents</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Uracile</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Chromatography, High Pressure Liquid</term><term>Light</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Photochemistry</term><term>Ultraviolet Rays</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Chromatographie en phase liquide à haute performance</term><term>Conformation moléculaire</term><term>Indicateurs et réactifs</term><term>Lumière</term><term>Modèles moléculaires</term><term>Oses acides</term><term>Photochimie</term><term>Potassium</term><term>Rayons ultraviolets</term><term>Sodium</term><term>Thymine</term><term>Uracile</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">To explore the structure-dependent hydrogen abstraction in antiparallel and parallel G-quartet DNA structures, the photochemical reactivity of 5-iodouracil ((I)U)-containing human telomeric DNA 22-mers was investigated under the 302 nm UV irradiation conditions. We discovered that only antiparallel ODN 4, in which the second T residue in the diagonal loop of the antiparallel G-quartet is substituted with (I)U, was rapidly consumed as compared with parallel ODN 4 and the other (I)U-containing 22-mers under the irradiation conditions. Product analysis of the photolyzate of antiparallel ODN 4 indicated that a 2'-deoxyribonolactone residue was effectively produced at the 5' side of the (I)U residue in the diagonal loop. Photochemical 2'-deoxyribonolactone formation was also found in the (I)U-containing diagonal loop of antiparallel G-quartets d(GGGGTTT(I)UGGGG)(2) and d(GGGGTT(I)UTGGGG)(2), whereas the reaction did not occur at other DNA structures, including the single-stranded form, the loop region of the hairpin, and linear four-stranded G-quartets. The results clearly indicate that this type of 2'-deoxyribonolactone formation efficiently occurrs only in the diagonal loop of the antiparallel G-quartet. Furthermore, we found that 2'-deoxyribonolactone was formed at the (I)U-containing G-rich sequence of the IgG switch regions and the 5' termini of the Rb gene, suggesting the formation of an antiparallel G-quartet with a diagonal loop in these sequences. These results suggest that the present photochemical method can be used as a specific probe for the antiparallel G-quartet with the diagonal loop.</div></front></TEI><affiliations><list><country><li>Japon</li></country><region><li>Région de Kantō</li></region><settlement><li>Tokyo</li></settlement></list><tree><noCountry><name sortKey="Sugiyama, Hiroshi" sort="Sugiyama, Hiroshi" uniqKey="Sugiyama H" first="Hiroshi" last="Sugiyama">Hiroshi Sugiyama</name></noCountry><country name="Japon"><region name="Région de Kantō"><name sortKey="Xu, Yan" sort="Xu, Yan" uniqKey="Xu Y" first="Yan" last="Xu">Yan Xu</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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