Uridine 2'-carbamates: facile tools for oligonucleotide 2'-functionalization.
A facile method for preparation of uridine 2'-carbamate derivatives based on reaction of 3',5'-disilyl-protected uridine with 1,1'-carbonyldiimidazole followed by treatment with an aliphatic amine is presented. A phosphoramidite monomer suitable for automated oligonucleotide synthesis is obtained in a few steps. The compounds are useful for the introduction of various labels and modifications into an oligonucleotide chain. Although 2'-carbamate modification is somewhat destabilizing for DNA-DNA and DNA-RNA duplexes, it is suitable for the direction of ligands into the minor groove of duplexes or at non-base-paired sites (e.g., loops and bulges) of oligonucleotides. Pyrene-modified oligonucleotide 2'-carbamates show a considerable increase in fluorescence intensity upon hybridization to a complementary RNA (but not DNA).
Korshun
Vladimir A
VA
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Moscow, Russia.
Stetsenko
Dmitry A
DA
Gait
Michael J
MJ
D000215:Acylation; D001483:Base Sequence; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D008954:Models, Biological; D009841:Oligonucleotides / Q000032:analysis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis; D014529:Uridine / Q000138:chemical synthesis / Q000737:chemistry*
D002219:Carbamates; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D014529:Uridine