Record Details

Influence of 2 '-Fluoro versus 2 '-O-Methyl Substituent on the Sugar Puckering of 4 '-C-Aminomethyluridine

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Influence of 2 '-Fluoro versus 2 '-O-Methyl Substituent on the Sugar Puckering of 4 '-C-Aminomethyluridine
 
Creator GORE, KR
HARIKRISHNA, S
PRADEEPKUMAR, PI
 
Subject FREE-ENERGY CALCULATIONS
NUCLEIC-ACIDS
MODIFIED OLIGONUCLEOTIDES
STRUCTURAL-PROPERTIES
FORCE-FIELD
RNA
DNA
NUCLEOSIDES
THERAPEUTICS
THYMIDINES
 
Description Herein, we report the synthesis of 4'-C-aminomethyl-2'-deoxy-2'-fluorouridine, a therapeutically appealing RNA modification. Conformational analysis by DFT calculations and molecular dynamics simulations using trinucleotide model systems revealed that modified sugar adopts C3'-endo conformation. In this conformer, a weak intramolecular C-H center dot center dot center dot F H-bond between the hydrogen atom of the 4'-C-CH2 group and the F atom at the 2' position is observed. Comparative studies with, unmodified, 2'-fluoro-, 2'-O-methyl-, and 4'-C-aminomethyl-2'-O-methyluridine showed the chemical nature of 2'-substituent dictates the sugar puckering of 2',4' modified nucleotides.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-16T13:25:58Z
2014-10-16T13:25:58Z
2013
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 78(19)9956-9962
http://dx.doi.org/10.1021/jo4012333
http://dspace.library.iitb.ac.in/jspui/handle/100/15661
 
Language en