New synthetic routes to synthons suitable for 2′-O-allyloligoribonucleotide assembly
Open Access
- 25 February 1991
- journal article
- research article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 19 (4) , 733-738
- https://doi.org/10.1093/nar/19.4.733
Abstract
New synthetic routes have been devised for the high yield preparation of protected 2′-O-allylribonucleoside- 3′4-phosphoramldites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-amlnoadenosine). 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 riboslde enables short 2′O-allyloligoribonucieotide probes to be synthesized with adenine replaced by 2-aminoadenlne. Thus very stable hybrids wtth complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amlno A-U base pairs.Keywords
This publication has 12 references indexed in Scilit:
- 2'-O-alkyl oligoribonucleotides as antisense probes.Proceedings of the National Academy of Sciences, 1990
- New synthetic routes to protected purine 2′-O-methylriboside-3′-O-phosphoramidites using a novel alkylation procedureNucleic Acids Research, 1990
- Prevention of chain cleavage in the chemical synthesis of 2′-silylated oligoribonucleotidesNucleic Acids Research, 1989
- Highly efficient chemical synthesis of 2′-O-methyloligoribonucleotides and tetrabiotinylated derivatives; novel probes that are resistant to degradation by RNA or DNA specific nucleasesNucleic Acids Research, 1989
- The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groupsNucleic Acids Research, 1987
- Synthesis of O2'-Methyluridine, O2'-Methylcytidine, N4,O2'-Dimethylcytidine and N4,N4,O2'-Trimethylcytidine from a Common Intermediate.Acta Chemica Scandinavica, 1986
- Polymer support oligonucleotide synthesis XVIII1.2): use ofβ-cyanoethyi-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final productNucleic Acids Research, 1984
- 2-Aminoadenine is an adenine substituting for a base in S-2L cyanophage DNANature, 1977
- The interaction of actinomycin with DNA: requirement for the 2-amino group of purines.Proceedings of the National Academy of Sciences, 1967
- Synthesis of 2'-O-Methyluridine, 2'-O-Methylcytidine and Their Relating Compounds.CHEMICAL & PHARMACEUTICAL BULLETIN, 1965