[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.
Zatsepin
T S
TS
Chemical Department and Belozersky Institute of Physicochemical Biology, Moscow State University, Vorob'evy gory, Moscow V-234, 119899 Russia.
Kachalova
A V
AV
Romanova
E A
EA
Stestenko
D A
DA
Gait
M J
MJ
Oretskaia
T S
TS
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