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. 1989 Apr 11;17(7):2379–2390. doi: 10.1093/nar/17.7.2379

Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection.

C Lehmann 1, Y Z Xu 1, C Christodoulou 1, Z K Tan 1, M J Gait 1
PMCID: PMC317630  PMID: 2717397

Abstract

Efficient solid-phase synthesis of a series of oligoribonucleotides of up to 20 residues is described that utilises the 9-fluorenylmethoxycarbonyl group (Fmoc) for 5'-protection and 4-methoxytetrahydropyran-4-yl (Mthp) for 2'-protection of ribonucleotide monomers and a phosphoramidite coupling procedure. The Fmoc group is removed after each coupling step by treatment with 0.1M DBU in acetonitrile. Oligoribonucleotides are isolated in 2'-protected form in good yield and shown to be readily and efficiently deprotected by mild acidic treatment.

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Selected References

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

  1. Fukuda T., Hamana T., Marumoto R. Synthesis of RNA oligomer using 9-fluorenylmethoxycarbonyl (Fmoc) group for 5'-hydroxyl protection. Nucleic Acids Symp Ser. 1988;(19):13–16. [PubMed] [Google Scholar]
  2. Iwai S., Ohtsuka E. 5'-Levulinyl and 2'-tetrahydrofuranyl protection for the synthesis of oligoribonucleotides by the phosphoramidite approach. Nucleic Acids Res. 1988 Oct 25;16(20):9443–9456. doi: 10.1093/nar/16.20.9443. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Ogilvie K. K., Usman N., Nicoghosian K., Cedergren R. J. Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity. Proc Natl Acad Sci U S A. 1988 Aug;85(16):5764–5768. doi: 10.1073/pnas.85.16.5764. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Reese C. B., Skone P. A. Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions. Nucleic Acids Res. 1985 Jul 25;13(14):5215–5231. doi: 10.1093/nar/13.14.5215. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. 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]
  6. 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]
  7. Stawinski J., Strömberg R., Thelin M., Westman E. Studies on the t-butyldimethylsilyl group as 2'-O-protection in oligoribonucleotide synthesis via the H-phosphonate approach. Nucleic Acids Res. 1988 Oct 11;16(19):9285–9298. doi: 10.1093/nar/16.19.9285. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Tanaka T., Tamatsukuri S., Ikehara M. Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2'-hydroxyl via a phosphite triester approach. Nucleic Acids Res. 1986 Aug 11;14(15):6265–6279. doi: 10.1093/nar/14.15.6265. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Tanaka T., Tamatsukuri S., Ikehara M. Solid phase synthesis of oligoribonucleotides using the o-nitrobenzyl group for 2'-hydroxyl protection and H-phosphonate chemistry. Nucleic Acids Res. 1987 Sep 25;15(18):7235–7248. doi: 10.1093/nar/15.18.7235. [DOI] [PMC free article] [PubMed] [Google Scholar]

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