Difluorophosphonylated Allylic Ether Moiety as a 2'-Modification of RNA-Type Molecules: Synthesis, Thermal, and Metabolic Studies.
Org Lett
; 21(12): 4803-4807, 2019 06 21.
Article
de En
| MEDLINE
| ID: mdl-31150255
ABSTRACT
The first synthesis of oligonucleotides incorporating URF, a uridine modified with a difluorophosphonylated allylic ether onto the 2'-position, is described. Fluorinated homouridylates and miR-342-3p analogues are efficiently prepared. UV-melting experiments and enzymatic degradation studies indicate this new series of fluorinated oligonucleotides exhibit good and thermal metabolic stability as well as an increased lipophilicity. Comparison with oligonucleotides containing 2'- O-allyluridine instead of URF reveals improvement of these chemical properties is related to the presence of the difluoromethylphosphonate group.
Texte intégral:
1
Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Température
/
Uridine
/
ARN
/
Composés allyliques
/
Éthers
Langue:
En
Journal:
Org Lett
Sujet du journal:
BIOQUIMICA
Année:
2019
Type de document:
Article
Pays d'affiliation:
France