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Oligonucleotides Functionalized by Fluorescein and Rhodamine Dyes: Michael Addition of Methyl Acrylate to 2′‐Deoxypseudouridine
Author(s) -
Ramzaeva Natalya,
Rosemeyer Helmut,
Leonard Peter,
Mühlegger Klaus,
Bergmann Frank,
von der Eltz Herbert,
Seela Frank
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9
Subject(s) - chemistry , phosphoramidite , oligonucleotide , fluorescence , thermal stability , derivative (finance) , methyl acrylate , absorbance , acrylate , fluorescein , polymer chemistry , stereochemistry , polymer , organic chemistry , chromatography , copolymer , dna , biochemistry , physics , quantum mechanics , financial economics , economics
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.