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. 1991 Feb 25;19(4):733–738. doi: 10.1093/nar/19.4.733

New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly.

B S Sproat 1, A M Iribarren 1, R G Garcia 1, B Beijer 1
PMCID: PMC333704  PMID: 1708121

Abstract

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.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Cerami A., Reich E., Ward D. C., Goldberg I. H. The interaction of actinomycin with DNA: requirement for the 2-amino group of purines. Proc Natl Acad Sci U S A. 1967 Apr;57(4):1036–1042. doi: 10.1073/pnas.57.4.1036. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Furukawa Y., Kobayashi K., Kanai Y., Honjo M. Synthesis of 2'-O-methyluridine, 2'-O-methylcytidine and their relating compounds. Chem Pharm Bull (Tokyo) 1965 Nov;13(11):1273–1278. doi: 10.1248/cpb.13.1273. [DOI] [PubMed] [Google Scholar]
  3. Howard F. B., Miles H. T. 2NH2A X T helices in the ribo- and deoxypolynucleotide series. Structural and energetic consequences of 2NH2A substitution. Biochemistry. 1984 Dec 18;23(26):6723–6732. doi: 10.1021/bi00321a068. [DOI] [PubMed] [Google Scholar]
  4. Iribarren A. M., Sproat B. S., Neuner P., Sulston I., Ryder U., Lamond A. I. 2'-O-alkyl oligoribonucleotides as antisense probes. Proc Natl Acad Sci U S A. 1990 Oct;87(19):7747–7751. doi: 10.1073/pnas.87.19.7747. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Kirnos M. D., Khudyakov I. Y., Alexandrushkina N. I., Vanyushin B. F. 2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA. Nature. 1977 Nov 24;270(5635):369–370. doi: 10.1038/270369a0. [DOI] [PubMed] [Google Scholar]
  6. Nyilas A., Chattopadhyaya J. Synthesis of O2'-methyluridine, O2'-methylcytidine, N4,O2'-dimethylcytidine and N4,N4,O2'-trimethylcytidine from a common intermediate. Acta Chem Scand B. 1986 Nov;40(10):826–830. doi: 10.3891/acta.chem.scand.40b-0826. [DOI] [PubMed] [Google Scholar]
  7. Pieles U., Sproat B. S., Lamm G. M. A protected biotin containing deoxycytidine building block for solid phase synthesis of biotinylated oligonucleotides. Nucleic Acids Res. 1990 Aug 11;18(15):4355–4360. doi: 10.1093/nar/18.15.4355. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Reese C. B., Stewart J. C., van Boom J. H., de Leeuw H. P., Nagel J., de Rooy J. F. The synthesis of oligoribonucleotides. Part XI. Preparation of ribonucleoside 2'-acetal 3'-esters by selective deacylation. J Chem Soc Perkin 1. 1975;(10):934–942. doi: 10.1039/p19750000934. [DOI] [PubMed] [Google Scholar]
  9. Schulhof J. C., Molko D., Teoule R. The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups. Nucleic Acids Res. 1987 Jan 26;15(2):397–416. doi: 10.1093/nar/15.2.397. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Sinha N. D., Biernat J., McManus J., Köster H. Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucleic Acids Res. 1984 Jun 11;12(11):4539–4557. doi: 10.1093/nar/12.11.4539. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Sproat B. S., Beijer B., Iribarren A. New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure. Nucleic Acids Res. 1990 Jan 11;18(1):41–49. doi: 10.1093/nar/18.1.41. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Sproat B. S., Lamond A. I., Beijer B., Neuner P., Ryder U. Highly efficient chemical synthesis of 2'-O-methyloligoribonucleotides and tetrabiotinylated derivatives; novel probes that are resistant to degradation by RNA or DNA specific nucleases. Nucleic Acids Res. 1989 May 11;17(9):3373–3386. doi: 10.1093/nar/17.9.3373. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Wu T., Ogilvie K. K., Pon R. T. Prevention of chain cleavage in the chemical synthesis of 2'-silylated oligoribonucleotides. Nucleic Acids Res. 1989 May 11;17(9):3501–3517. doi: 10.1093/nar/17.9.3501. [DOI] [PMC free article] [PubMed] [Google Scholar]

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