Studies on transfer ribonucleic acids and related compounds. IX. Ribooligonucleotide synthesis using a photosensitive o-nitrobenzyl protection at the 2'-hydroxyl group.
o-Nitrobenzyl group was introduced to the 2'-hydroxyl function of uridine via 2',3'-O-(dibutylstannylene) uridine. The benzylated uridine was protected at the 5'-hydroxyl group with monomethoxytrityl chloride and condensed with 2',3'-O-dibenzoyluridine 5'-phosphate or N,N',2',3'-O-tetrabenzoyladenosine 5'-phosphate using dicyclohexylcarbodiimide (DCC). o-Nitrobenzyl ether linkage of the dinucleotides was removed by UV irradiation with wavelength longer than 320 nm. Deprotected UpU and UpA thus obtained were characterized by RNase A digestion.
Ohtsuka
E
E
Tanaka
S
S
Ikehara
M
M
D002854:Chromatography, Paper; D004987:Ethers / Q000737:chemistry / Q000528:radiation effects; D009682:Magnetic Resonance Spectroscopy; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009947:Organotin Compounds / Q000737:chemistry*; D010777:Photochemistry; D012343:RNA, Transfer / Q000737:chemistry*; D014466:Ultraviolet Rays; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
C408288:2',3'-O-(dibutylstannylene)uridine; C408287:2'-O-(o-nitrobenzyl)uridine; D004987:Ethers; D009578:Nitrobenzenes; D009843:Oligoribonucleotides; D009947:Organotin Compounds; D012343:RNA, Transfer; D014529:Uridine