Oligonucleotides functionalized by fluorescein and rhodamine dyes: Michael addition of methyl acrylate to 2 `-deoxypseudouridine

Autor(en): Ramzaeva, N
Rosemeyer, H 
Leonard, P
Muhlegger, K
Bergmann, F
von der Eltz, H
Seela, F
Stichwörter: C-NUCLEOSIDES; Chemistry; Chemistry, Multidisciplinary; EQUILIBRIUM; OLIGODEOXYRIBONUCLEOTIDES; PAIR; PSI-URIDINE; RECOGNITION
Erscheinungsdatum: 2000
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: HELVETICA CHIMICA ACTA
Volumen: 83
Ausgabe: 6
Startseite: 1108
Seitenende: 1126
Zusammenfassung: 
The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.
ISSN: 0018019X
DOI: 10.1002/1522-2675(20000607)83:6<1108::AID-HLCA1108>3.0.CO;2-9

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