학술논문

Synthesis and Duplex‐Stabilizing Properties of Fluorinated N‐Methanocarbathymidine Analogues Locked in the C3′‐endo Conformation
Document Type
article
Source
Angewandte Chemie International Edition. 53(37)
Subject
Organic Chemistry
Chemical Sciences
Models
Molecular
Molecular Conformation
Molecular Structure
Nucleic Acid Conformation
Oligonucleotides
Thymidine
asymmetric synthesis
diastereoselectivity
duplex thermal stability
fluorination
modified nucleosides
Asymmetric synthesis
Diastereoselectivity
Duplex thermal stability
Fluorination
Modified nucleosides
Chemical sciences
Language
Abstract
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.