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LNA guanine and 2,6-diaminopurine. Synthesis, characterization and hybridization properties of LNA 2,6-diaminopurine containing oligonucleotides

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningfagfællebedømt

  • C. Rosenbohm
  • Daniel Sejer Pedersen
  • M. Frieden
  • F.R. Jensen
  • T. Koch
  • S. Arent
  • S. Larsen
LNA guanine and 2,6-diaminopurine (D) phosphoramidites have been synthesized as building blocks for antisense oligonucleotides (ON). The effects of incorporating LNA D into ON were investigated. As expected, LNA D containing ON showed increased affinity towards complementary DNA (ΔT +1.6 to +3.0°C) and RNA (ΔT +2.6 to +4.6°C) ON. To evaluate if LNA D containing ON have an enhanced mismatch sensitivity compared to their complementary LNA A containing ON thermal denaturation experiments towards singly mismatched DNA and RNA ON were undertaken. Replacing one LNA A residue with LNA D, in fully LNA modified ON, resulted in higher mismatch sensitivity towards DNA ON (ΔΔT -4 to >-17°C). The same trend was observed towards singly mismatched RNA ON (ΔΔT D-a = -8.7°C and D-g = -4.5°C) however, the effect was less clearcut and LNA A showed a better mismatch sensitivity than LNA D towards cytosine (ΔT +5.5°C). © 2004 Elsevier Ltd. All rights reserved.
OriginalsprogEngelsk
TidsskriftBioorganic and Medicinal Chemistry
Vol/bind12
Udgave nummer9
Sider (fra-til)2385-2396
Antal sider12
ISSN0968-0896
DOI
StatusUdgivet - 1 maj 2004
Eksternt udgivetJa

ID: 50628809