Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers
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Description
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 ¢Tm of +2.4 to -8.1
°C/modification relative to unmodified PNA.
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 ¢Tm of +2.4 to -8.1
°C/modification relative to unmodified PNA.
Date of Publication
2003
Publication Type
Article
Subject(s)
Language(s)
en
Additional Credits
Series
Organic letters
Publisher
American Chemical Society
ISSN
1523-7060
Access(Rights)
metadata.only