New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly.
New synthetic routes have been devised for the high yield preparation of protected 2'-O-allylribonucleoside-3'-O-phosphoramidites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-aminoadenosine). Key features are the use of versatile intermediates and an easy allylation step. The development of a novel synthon based on 2'-O-allyl-2,6-diaminopurine riboside enables short 2'-O-allyl-oligoribonucleotide probes to be synthesized with adenine replaced by 2-aminoadenine. Thus very stable hybrids with complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amino A.U base pairs.
Sproat
B S
BS
European Molecular Biology Laboratory, Heidelberg, FRG.
Iribarren
A M
AM
Garcia
R G
RG
Beijer
B
B
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D055598:Chemical Phenomena; D002621:Chemistry; D007202:Indicators and Reagents; D009843:Oligoribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis*
D000498:Allyl Compounds; D007202:Indicators and Reagents; D009843:Oligoribonucleotides; D012313:RNA