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Deoxyribo‐ and Ribonucleoside H‐Phosphonates

dc.contributor.authorStawinski, Jacek
dc.contributor.authorStrömberg, Roger
dc.date.accessioned2018-05-15T20:14:33Z
dc.date.available2018-05-15T20:14:33Z
dc.date.issued2001-04
dc.identifier.citationStawinski, Jacek; Strömberg, Roger (2001). "Deoxyribo‐ and Ribonucleoside H‐Phosphonates." Current Protocols in Nucleic Acid Chemistry 4(1): 2.6.1-2.6.15.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/143703
dc.description.abstractMost methods for preparing H‐phosphonate monoesters suffer from variable yields and are often incompatible with common protecting groups used in oligonucleotide synthesis. This unit describes four procedures that consistently give high yields of the desired products. Taken together, they provide an arsenal of phosphonylation prodecures that it compatible with most common protecting groups.
dc.publisherHumana Press
dc.publisherWiley Periodicals, Inc.
dc.titleDeoxyribo‐ and Ribonucleoside H‐Phosphonates
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.subject.hlbtoplevelEngineering
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/143703/1/cpnc0206.pdf
dc.identifier.doi10.1002/0471142700.nc0206s04
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceFroehler et al., 1986.See above.
dc.identifier.citedreferenceStawinski, J. and Strömberg, R. 1993. H‐Phosphonates in Oligonucleotide Synthesis. Trends Org. Chem. 4: 31 ‐ 67.
dc.identifier.citedreferenceStawinski, J. 1992. Some Aspects of H‐Phosphonate Chemistry. In Handbook of Organophosphorus Chemistry ( R. Engel ed.) pp. 377 ‐ 434. Marcel Dekker, New York.
dc.identifier.citedreferenceMarugg et al., 1986.See above.
dc.identifier.citedreferenceJankowska et al., 1994.See above.
dc.identifier.citedreferenceWada, T., Sato, Y., Honda, F., Kawahara, S., and Sekine, M. 1997. Chemical synthesis of oligodeoxyribonucleotides using N‐unprotected H‐phosphonate monomers and carbonium and phosphonium condensing reagents: O‐Selective phosphonylation and condensation. J. Am. Chem. Soc. 119: 12710 ‐ 12721.
dc.identifier.citedreferenceYoung, R.W. 1952. A re‐examination of the reaction between phosphorus trichloride and salicylic acid. J. Am. Chem. Soc. 74: 1672 ‐ 1673.
dc.identifier.citedreferenceZhang, X., Abad, J.‐L., Huang, Q., Zeng, F., Gaffney, B., and Jones, R. 1997. High yield protection of purine ribonucleosides for H‐phosphonate RNA synthesis. Tetrahedron. Lett. 38: 7135 ‐ 7138.
dc.identifier.citedreferenceGaregg et al., 1986c.See above.
dc.identifier.citedreferenceStawinski and Thelin, 1990a.See above.
dc.identifier.citedreferenceStawinski et al., 1988.See above.
dc.identifier.citedreferenceRozners et al., 1995b.See above.
dc.identifier.citedreferenceBhongle, N.N. and Tang, J.Y. 1995. A convenient synthesis of nucleoside 3′‐H‐phosphonate monoesters using triphosgene. Tetrahedron Lett. 36: 6803 ‐ 6806.
dc.identifier.citedreferenceFroehler, B.C. 1993. Oligodeoxynucleotide synthesis. H‐Phosphonate approach. In Protocols for Oligonucleotides and Analogs ( S. Agrawal ed.) pp. 63 ‐ 80. Humana Press, Totowa, N.J.
dc.identifier.citedreferenceFroehler, B.C., Ng, P.G., and Matteucci, M.D. 1986. Synthesis of DNA via deoxynucleoside H‐phosphonate intermediates. Nucl. Acids Res. 14: 5399 ‐ 5407.
dc.identifier.citedreferenceGaffney, B.L. and Jones, R.A. 1988. Large‐scale oligonucleotide synthesis by the H‐phosphonate method. Tetrahedron Lett. 29: 2619 ‐ 2622.
dc.identifier.citedreferenceGaregg, P.J., Regberg, T., Stawinski, J., and Strömberg, R. 1985. Formation of internucleotidic bond via phosphonate intermediates. Chem. Scr. 25: 280 ‐ 282.
dc.identifier.citedreferenceGaregg, P.J., Lindh, I., Regberg, T., Stawinski, J., Strömberg, R., and Henrichson, C. 1986a. Nucleoside H‐Phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 27: 4051 ‐ 4054.
dc.identifier.citedreferenceGaregg, P.J., Lindh, I., Regberg, T., Stawinski, J., Strömberg, R., and Henrichson, C. 1986b. Nucleoside H‐phosphonates. IV. Automated solid Phase synthesis of oligoribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 27: 4055 ‐ 4058.
dc.identifier.citedreferenceGaregg, P.J., Regberg, T., Stawinski, J., and Strömberg, R. 1986c. Nucleoside hydrogenphosphonates in oligonucleotide synthesis. Chem. Scr. 26: 59 ‐ 62.
dc.identifier.citedreferenceGaregg, P.J., Stawinski, J., and Strömberg, R. 1987. Activation of nucleoside hydrogenphosphonates by use of aryl sulfonyl chlorides. Nucleosides Nucleotides 6: 425 ‐ 427.
dc.identifier.citedreferenceGibbs, D.E. and Larsen, C. 1984. Bis[2,2,2‐trifluoroethyl] phosphite, a new reagent for synthesizing mono‐ and diesters of phosphorus acid. Synthesis (1984): 410 ‐ 413.
dc.identifier.citedreferenceHall, R.H., Todd, A., and Webb, R.F. 1957. Nucleotides. Part XLI. Mixed anhydrides as intermediates in the synthesis of dinucleoside phosphates. J. Chem. Soc. (1957): 3291 ‐ 3296.
dc.identifier.citedreferenceHata, T. and Sekine, M. 1974. Oxidation of nucleoside phosphites by means of 2,2′‐dipyridilyl disulfide via nucleoside silylphosphite intermediates. Tetrahedron Lett. (1974): 3943 ‐ 3946.
dc.identifier.citedreferenceHoly, A. and Smrt, J. 1966. Oligonucleotidic compounds. XI. Synthesis of ribonucleoside 2′,3′‐cyclophosphates from nucleosides via nucleoside 2′,3′‐phosphites. Collect. Czech. Chem. Commun. 31: 1528 ‐ 1534.
dc.identifier.citedreferenceHoly, A. and Sorm, F. 1966. Nucleic acids components and their analogues. LXXX. Preparation of nucleoside phosphites by the reaction of nucleosides with triphenyl phosphites. collect. Czech. Chem. Commun. 31: 1544 ‐ 1561.
dc.identifier.citedreferenceHoly, A., Smrt, J., and Sorm, F. 1965. Nucleic acids components and their analogues. LIX. The preparation and properties of nucleoside phosphites. Collect. Czech. Chem. Commun. 30: 1635 ‐ 1641.
dc.identifier.citedreferenceHonjo, M., Marumoto, R., Kobayashi, K., and Yoshioka, Y. 1966. Phosphorylation of ribonucleosides with phosphorus trichloride. Tetrahedron Lett. (1966): 3851 ‐ 3856.
dc.identifier.citedreferenceJankowska, J., Sobkowski, M., Stawinski, J., and Kraszewski, A. 1994. Studies on aryl H‐phosphonates. I. Efficient method for the preparation of deoxyribo‐ and ribonucleoside 3′‐H‐phosphonate monoesters by transesterification of diphenyl H‐phosphonate. Tetrahedron Lett. 35: 3355 ‐ 3358.
dc.identifier.citedreferenceKers, A., Kers, I., Stawinski, J., Sobkowski, M., and Kraszewski, A. 1996. Studies on aryl H‐phosphonates. 3. Mechanistic investigations related to the disproportionation of diphenyl H‐phosphonate under anhydrous basic conditions. Tetrahedron 52: 9931 ‐ 9944.
dc.identifier.citedreferenceMarugg, J.E., Tromp, M., Kuyl‐ Yeheskiely, E., van der Marel, G.A., and van Boom, J.H. 1986. A convenient and general approach to the synthesis of properly protected d‐nucleoside‐3′ hydrogenphosphonates via phosphite intermediates. Tetrahedron Lett. 27: 2661 ‐ 2664.
dc.identifier.citedreferenceMcConnell, R.L. and Coover, H.W. 1959. Phosphorus‐containing derivatives of 2,2‐dimethyl‐1,3‐propanediol. Org. Chem. 24: 630 ‐ 635.
dc.identifier.citedreferenceOzola, V., Reese, C.B., and Song, Q.L. 1996. Use of ammonium aryl H ‐phosphonates in the preparation of nucleoside H‐phosphonate building blocks. Tetrahedron Lett. 37: 8621 ‐ 8624.
dc.identifier.citedreferenceRozners, E. and Strömberg, R. 1997. Synthesis and properties of oligoribonucleotide analogs having formacetal internucleoside linkages. J. Org. Chem. 62: 1846 ‐ 1850.
dc.identifier.citedreferenceRozners, E., Kumpins, V., Rekis, A., and Bizdena, E. 1998. Solid phase synthesis of oligoribonucleotides by the H‐phosphonate method using 2′‐O‐benzoyl protective group. Bioorg. Khim. 14: 1580 ‐ 1582.
dc.identifier.citedreferenceRozners, E., Rekis, A., Kumpins, V., and Bizdena, E. 1990. Synthesis of oligoribonucleotides by the H‐phosphonate method using base‐labile 2′‐O‐protecting groups. II. Some aspects of use of 2′‐O‐benzoyl and anisoyl protecting groups. Bioorg. Khim. 16: 1531 ‐ 1536.
dc.identifier.citedreferenceRozners, E., Renhofa, R., Petrova, M., Popelis, J., Kumpins, V., and Bizdena, E. 1992. Synthesis of oligoribonucleotides by the H‐phosphonate approach using base labile 2′‐O‐protecting groups. 5. Recent progress in development of the method. Nucleosides Nucleotides 11: 1579 ‐ 1593.
dc.identifier.citedreferenceRozners, E., Strömberg, R., and Bizdena, E. 1995a. Synthesis of oligoarabinonucleotides using H‐phosphonates. Nucleosides Nucleotides 14: 851 ‐ 853.
dc.identifier.citedreferenceRozners, E., Strömberg, R., and Bizdena, E. 1995b. Synthesis of RNA fragments using the H‐phosphonate method and 2′‐(2‐chlorobenzoyl) protection. Nucleosides Nucleotides 14: 855 ‐ 857.
dc.identifier.citedreferenceSchofield, J.A. and Todd, A. 1961. Nucleotides. Part XLVI. A new method for the preparation of nucleoside phosphites. J. Chem. Soc. (1961): 2316 ‐ 2320.
dc.identifier.citedreferenceSekine, M. and Hata, T. 1975. Phenylthio group as a protecting group of phosphates in oligonucleotide synthesis via phosphotriester approach. Tetrahedron Lett. (1975): 1711 ‐ 1714.
dc.identifier.citedreferenceSekine, M., Mori, H., and Hata, T. 1979. New type of chemical oxidative phosphorylation: Activation of phosphonate function by use of triisopropylbenzenesulfonyl chloride. Tetrahedron Lett. (1979): 1145 ‐ 1148.
dc.identifier.citedreferenceSekine, M., Narui, S., and Hata, T. 1988. A convenient method for the synthesis of deoxyribonucleoside 3′‐hydrogenphosphonates. Tetrahedron Lett. 29: 1037 ‐ 1040.
dc.identifier.citedreferenceStawinski, J. and Thelin, M. 1990a. Nucleoside H‐Phosphonates. XI. A convenient method for the preparation of nucleoside H‐phosphonates. Nucleosides Nucleotides 9: 129 ‐ 135.
dc.identifier.citedreferenceStawinski, J. and Thelin, M. 1990b. Studies on the activation pathway of phosphonic acid using acyl chlorides as activators. J. Chem. Soc. Perkin Trans. 2. (1990): 849 ‐ 853.
dc.identifier.citedreferenceStawinski, J., Strömberg, R., Thelin, M., and Westman, E. 1988. Studies on the t‐butyldimethylsilyl group as 2′‐O‐protection in oligoribonucleotide synthesis via the H‐phosphonate approach. Nucl. Acids Res. 16: 9285 ‐ 9298.
dc.identifier.citedreferenceSzabò, T., Almer, H., Strömberg, R., and Stawinski, J. 1995. 2‐Cyanoethyl H‐phosphonate. A reagent for the mild preparation of nucleoside H‐phosphonate monoesters. Nuceosides Nucleotides 4: 715 ‐ 716.
dc.identifier.citedreferenceTakaku, H., Yamakage, S., Sakatsume, O., and Ohtsuki, M. 1988. A convenient approach to the synthesis of deoxyribonucleoside 3′‐hydrogenphosphonates via bis(1,1,1,3,3,3‐hexafluoro‐2‐propyl) phosphonate intermediate. Chem. Lett. (1988): 1675 ‐ 1678.
dc.owningcollnameInterdisciplinary and Peer-Reviewed


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