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dc.contributor.author
Taverna Porro, Marisa Lia
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dc.contributor.author
Saint Pierre, Christine
dc.contributor.author
Gasparutto, Didier
dc.contributor.author
Ravanat, Jean Luc
dc.date.available
2021-09-08T15:00:27Z
dc.date.issued
2020-01
dc.identifier.citation
Taverna Porro, Marisa Lia; Saint Pierre, Christine; Gasparutto, Didier; Ravanat, Jean Luc; Solid-phase synthesis of branched oligonucleotides containing a biologically relevant dCyd341 interstrand crosslink DNA lesion; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 18; 10; 1-2020; 1892-1899
dc.identifier.issn
1477-0520
dc.identifier.uri
http://hdl.handle.net/11336/139898
dc.description.abstract
Branched oligonucleotides containing a biologically relevant DNA lesion, dCyd341, which involves an interstrand crosslink between a cytosine base on one strand and a ribose moiety on the opposite strand, were prepared in a single automated solid-phase synthesis. For this, we first prepared the phosphoramidite analogue of dCyd341 bearing an orthogonal levulinyl protecting group. Then, following the synthesis of the first DNA strand containing dCyd341, the levulinic group was removed and the synthesis was then continued from the free base hydroxyl group at the branching point, using traditional phosphoramidites. The synthesized oligonucleotides were fully characterized by MALDI-TOF/MS and were enzymatically digested, and the presence of the lesion was confirmed by HPLC-MS/MS and the sequence was finally controlled upon exonuclease digestion followed by MALDI-TOF/MS analysis. The developed strategy was successfully employed for the preparation of several short linear and branched oligonucleotides containing the aforementioned lesion.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Royal Society of Chemistry
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dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
BRANCHED OLIGONUCLEOTIDE
dc.subject
INTERSTRAND CROSS-LINKS
dc.subject
DNA DAMAGE
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Solid-phase synthesis of branched oligonucleotides containing a biologically relevant dCyd341 interstrand crosslink DNA lesion
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2021-09-07T19:20:45Z
dc.journal.volume
18
dc.journal.number
10
dc.journal.pagination
1892-1899
dc.journal.pais
Reino Unido
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dc.journal.ciudad
Cambridge
dc.description.fil
Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Química y Metabolismo del Fármaco. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Instituto de Química y Metabolismo del Fármaco; Argentina
dc.description.fil
Fil: Saint Pierre, Christine. Universite Grenoble Alpes; Francia
dc.description.fil
Fil: Gasparutto, Didier. Universite Grenoble Alpes; Francia
dc.description.fil
Fil: Ravanat, Jean Luc. Universite Grenoble Alpes; Francia
dc.journal.title
Organic & Biomolecular Chemistry
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://xlink.rsc.org/?DOI=C9OB01021A
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1039/C9OB01021A
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