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2′-Lipid-modified oligonucleotides via a ‘Staudinger–Vilarrasa’ reaction

✍ Scribed by Hubert Chapuis; Laurent Bui; Isabelle Bestel; Philippe Barthélémy

Book ID
104095843
Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
146 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

We report a new access to 2 0 -amido-2 0 -deoxyuridine via a Staudinger-Vilarrasa coupling reaction for the preparation of lipid-modified oligonucleotides. One or two lipidic moieties were inserted within the oligonucleotidic sequence (LONs) leading to a repertoire of original antagomir-like molecules targeting micro RNA (miRNA or miR). Melting temperature (Tm) experiments revealed that the stability of the duplexes depends on the lipid position and the number of lipid moieties inserted within the oligonucleotide sequence. Single lipid conjugations of positions 11 and 19 of LONs targeting miR-122 do not destabilize the duplexes.

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