Premium
Synthesis and Duplex‐Stabilizing Properties of Fluorinated N ‐Methanocarbathymidine Analogues Locked in the C3′‐ endo Conformation
Author(s) -
Jung Michael E.,
Dwight Timothy A.,
Vigant Frederic,
Østergaard Michael E.,
Swayze Eric E.,
Seth Punit P.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405283
Subject(s) - duplex (building) , chemistry , thermal stability , stereochemistry , combinatorial chemistry , dna , organic chemistry , biochemistry
The efficient synthesis, antiviral activity, and duplex‐stabilizing properties of both isomers of the 2′‐fluoro analogue of Northern methanocarbathymidine (N‐MCT), 2 and 3 , are reported. We show that 2′‐F incorporation on the N‐MCT scaffold has a strong stabilizing effect on duplex thermal stability.