Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

Leumann, Christian (2003). Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers. Organic letters, 5(11), pp. 1987-1990. American Chemical Society

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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.

Item Type:	Journal Article (Original Article)
Division/Institute:	08 Faculty of Science > Department of Chemistry, Biochemistry and Pharmaceutical Sciences (DCBP)
UniBE Contributor:	Leumann, Christian
Subjects:	500 Science > 570 Life sciences; biology 500 Science > 540 Chemistry
ISSN:	1523-7060
Publisher:	American Chemical Society
Language:	English
Submitter:	Marcel Hollenstein
Date Deposited:	23 Apr 2015 12:47
Last Modified:	05 Dec 2022 14:45
URI:	https://boris.unibe.ch/id/eprint/67218