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© Research
Publication : Organic letters

Synthesis and incorporation into PNA of fluorinated olefinic PNA (F-OPA) monomers

Team: Bioorganic chemistry of nucleic acids
Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Organic letters - 29 May 2003

Hollenstein M, Leumann CJ

Link to Pubmed [PMID] – 12762703

Org. Lett. 2003 May;5(11):1987-90

[structure: see text] A fluorinated OPA monomer containing the base thymine ((Z)-t-F-OPA) was synthesized in 12 steps, featuring a highly selective allylic over homoallylic Mitsunobu substitution for the introduction of the nucleobase. F-OPA modified PNA decamers were prepared by the MMTr/acyl protection strategy. The thermal stability of duplexes of PNA decamers containing (Z)-t-F-OPA units with antiparallel complementary DNA was measured. We found a strong dependence of stability from the sequential position of the (Z)-t-F-OPA units, ranging from DeltaT(m) of +2.4 to -8.1 degrees C/modification relative to unmodified PNA.