[Synthesis and characteristics of modified oligodeoxyribonucleotides containing 2'-O-(2,3-dihydroxypropyl)uridine and 2'-O-(2-exoethyl)uridine].
A new uridine derivative, 2'-O-(2,3-dihydroxypropyl)uridine, and its 3'-phosphoramidite were obtained for direct introduction into oligonucleotides during automated chemical synthesis. Oligonucleotides 10 to 15 nt long harboring 2'-O-(2,3-dihydroxypropyl)uridine residues were synthesized; periodate oxidation of these oligomers gave oligonucleotides containing 2'-O-(2-oxoethyl)uridine residues. The presence of a reactive aldehyde group in 2' position of the carbohydrate moiety was confirmed by the interaction with p-nitrophenylhydrazine and methionine methyl ester. The thermostability of DNA duplexes containing modified units is practically indistinguishable from that of the natural analogues.
Chemical Department and Belozersky Institute of Physicochemical Biology, Moscow State University, Vorob'evy gory, Moscow V-234, 119899 Russia.
T S
TS
Zatsepin
A V
AV
Kachalova
E A
EA
Romanova
D A
DA
Stestenko
M J
MJ
Gait
T S
TS
Oretskaia
D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
C425964:2'-O-(2,3-dihydroxypropyl)uridine; C425965:2'-O-(2-oxoethyl)uridine; D009841:Oligonucleotides; D014529:Uridine