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Chemical Synthesis of RNA Sequences with 2′‐O‐[(Triisopropylsilyl)oxy]methyl‐protected Ribonucleoside Phosphoramidites

dc.contributor.authorPitsch, Stefan
dc.contributor.authorWeiss, Patrick A.
dc.date.accessioned2020-01-13T15:21:15Z
dc.date.available2020-01-13T15:21:15Z
dc.date.issued2001-12
dc.identifier.citationPitsch, Stefan; Weiss, Patrick A. (2001). "Chemical Synthesis of RNA Sequences with 2′‐O‐[(Triisopropylsilyl)oxy]methyl‐protected Ribonucleoside Phosphoramidites." Current Protocols in Nucleic Acid Chemistry 7(1): 3.8.1-3.8.15.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/153249
dc.description.abstractThe [(triisopropylsilyl)oxy]methyl (TOM) group is a useful protecting group for the 2′‐OH of ribonucleosides to be used for oligoribonucleotide synthesis by the phosphoramidite method. It is completely stable to all reaction conditions applied during assembly and the first deprotection step. It does not interfere with the coupling reaction and leads to very good coupling yields under DNA‐coupling conditions. The final cleavage occurs quantitatively without concomitant destruction of the RNA product. This unit describes the synthesis of TOM‐phosphoramidites from 2′‐O‐TOM‐5′‐O‐dimethoxytrityl‐N‐acetyl ribonucleosides, oligoribonucleotide assembly on an automated DNA synthesizer, and subsequent deprotection. Preparation of the TOM‐protected ribonucleosides is presented elsewhere in the series.
dc.publisherOxford University Press
dc.publisherWiley Periodicals, Inc.
dc.titleChemical Synthesis of RNA Sequences with 2′‐O‐[(Triisopropylsilyl)oxy]methyl‐protected Ribonucleoside Phosphoramidites
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.subject.hlbtoplevelEngineering
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/153249/1/cpnc0308.pdf
dc.identifier.doi10.1002/0471142700.nc0308s07
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceScaringe, S.A., Wincott, F.E., and Caruthers, M.H. 1998. Novel RNA synthesis method using 5′‐ O ‐silyl‐2′‐ O ‐orthoester protecting groups. J. Am. Chem. Soc. 120: 11820 ‐ 11821.
dc.identifier.citedreferenceSchwartz, M.E., Breaker, R.R., Asteriadis, G.T., deBear, J.S., and Gough, G.R. 1992. Rapid synthesis of oligoribonucleotides using 2′‐ O ‐(ortho‐nitrobenzyloxymethyl)‐protec ted monomers. Bioorg. Med. Chem. Lett. 2: 1019 ‐ 1024.
dc.identifier.citedreferenceBeaucage, S.L. and Caruthers, M.H. 1996. The chemical synthesis of DNA/RNA. In Bioorganic Chemistry: Nucleic Acids ( S.M. Hecht, ed.) pp. 36 ‐ 74. Oxford University Press, Oxford.
dc.identifier.citedreferenceGriffin, B.E. and Reese, C.B. 1964. Oligoribonucleotide synthesis via 2′,5′‐protected ribonucleoside derivatives. Tetrahedron Lett. 5: 2925 ‐ 2931.
dc.identifier.citedreferenceHogrefe, R.I., McCaffrey, A.P., Borozdine, L.U., McCampbell, E.S., and Vaghefi, M.M. 1993. Effect of excess water on the desilylation of oligoribonucleotides using tetrabutylammonium fluoride. Nucl. Acids Res. 21: 4739 ‐ 4741.
dc.identifier.citedreferenceOgilvie, K.K., Sadana, K.L., Thompson, E.A., Quilliam, M.A., and Westmore, J.B. 1974. The use of silyl protecting groups in protecting the hydroxyl functions of ribonucleosides. Tetrahedron Lett. 15: 2861 ‐ 2863.
dc.identifier.citedreferenceOhtsuka, E., Tanaka, S., and Ikehara, M. 1974. Ribooligonucleotide synthesis using a photosensitive o ‐nitrobenzyl protection at the 2′‐hydroxyl group. Nucl. Acids Res. 1: 1351 ‐ 1357.
dc.identifier.citedreferencePitsch, S. 1997. An efficient synthesis of enantiomeric oligoribonucleotides from D‐glucose. Helv. Chim. Acta 80: 2286 ‐ 2314.
dc.identifier.citedreferencePitsch, S., Weiss, P.A., Wu, X., Ackermann, D., and Honegger, T. 1999a. Fast and reliable automated synthesis of RNA and partially 2′‐ O ‐protected precursors (‘caged RNA’) based on two novel, orthogonal 2′‐ O ‐protecting groups. Helv. Chim. Acta 82: 1753 ‐ 1761.
dc.identifier.citedreferencePitsch, S., Weiss, P.A., and Jenny, L. Nov. 1999b. Ribonucleoside‐derivative and method for preparing the same. US Patent 5,986,084.
dc.identifier.citedreferencePitsch, S., Weiss, P.A., Jenny, L., Stutz, A., and Wu, X. 2001. Reliable chemical synthesis of oligoribonucleotides (RNA) with 2′‐ O ‐[(triisopropylsilyl)oxy]methyl (2′‐ O ‐TOM) protected phosphoramidites. Helv. Chim. Acta In press.
dc.identifier.citedreferenceReese, C.B., Rao, M.V., Serafinowska, H.T., Thompson, E.A., and Yu, P.S. 1991. Studies in the solid phase synthesis of oligo‐ and poly‐ribonucleotides. Nucleosides Nucleotides 10: 81 ‐ 97.
dc.identifier.citedreferenceUsman, N., Pon, R.T., and Ogilvie, K.K. 1985. Preparation of ribonucleoside 3′‐ O ‐phosphoramidites and their application to the automated solid‐phase synthesis of oligonucleotides. Tetrahedron Lett. 26: 4567 ‐ 4570.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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