Abstract
Galactose-modified thymidine, LNA-T and 2'-amino-LNA-T nucleosides were synthesized, converted into the corresponding phosphoramidite derivatives and introduced into short oligonucleotides. Compared to the unmodified control strands, the galactose-modified oligonucleotides in general, and the N2'-functionalized 2'-amino-LNA derivatives in particular, showed improved duplex thermal stability against DNA and RNA complements and increased ability to discriminate mismatches. In addition, especially the 2'-amino-LNA-T derivatives induced remarkable 3'-exonucleolytic stability. These results were further investigated using molecular modelling studies.
| Original language | English |
|---|---|
| Journal | The Journal of Organic Chemistry |
| Volume | 81 |
| Issue number | 22 |
| Pages (from-to) | 10845-10856 |
| ISSN | 0022-3263 |
| DOIs | |
| Publication status | Published - 13. Oct 2016 |
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Synthesis and Biophysical Investigations of Oligonucleotides Containing Galactose-Modified DNA, LNA and 2'-Amino-LNA Monomers. / Ries, Annika; Kumar, Rajesh; Lou, Chenguang; Kosbar, Tamer; Vengut-Climent, Empar; Jørgensen, Per Trolle; Morales, Juan C; Wengel, Jesper.
In: The Journal of Organic Chemistry, Vol. 81, No. 22, 13.10.2016, p. 10845-10856.Research output: Contribution to journal › Journal article › Research › peer-review
TY - JOUR
T1 - Synthesis and Biophysical Investigations of Oligonucleotides Containing Galactose-Modified DNA, LNA and 2'-Amino-LNA Monomers
AU - Ries, Annika
AU - Kumar, Rajesh
AU - Lou, Chenguang
AU - Kosbar, Tamer
AU - Vengut-Climent, Empar
AU - Jørgensen, Per Trolle
AU - Morales, Juan C
AU - Wengel, Jesper
PY - 2016/10/13
Y1 - 2016/10/13
N2 - Galactose-modified thymidine, LNA-T and 2'-amino-LNA-T nucleosides were synthesized, converted into the corresponding phosphoramidite derivatives and introduced into short oligonucleotides. Compared to the unmodified control strands, the galactose-modified oligonucleotides in general, and the N2'-functionalized 2'-amino-LNA derivatives in particular, showed improved duplex thermal stability against DNA and RNA complements and increased ability to discriminate mismatches. In addition, especially the 2'-amino-LNA-T derivatives induced remarkable 3'-exonucleolytic stability. These results were further investigated using molecular modelling studies.
AB - Galactose-modified thymidine, LNA-T and 2'-amino-LNA-T nucleosides were synthesized, converted into the corresponding phosphoramidite derivatives and introduced into short oligonucleotides. Compared to the unmodified control strands, the galactose-modified oligonucleotides in general, and the N2'-functionalized 2'-amino-LNA derivatives in particular, showed improved duplex thermal stability against DNA and RNA complements and increased ability to discriminate mismatches. In addition, especially the 2'-amino-LNA-T derivatives induced remarkable 3'-exonucleolytic stability. These results were further investigated using molecular modelling studies.
U2 - 10.1021/acs.joc.6b01917
DO - 10.1021/acs.joc.6b01917
M3 - Journal article
C2 - 27736097
VL - 81
SP - 10845
EP - 10856
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -