Show simple item record

Synthetic Strategies and Parameters Involved in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method

dc.contributor.authorBeaucage, Serge L.
dc.contributor.authorCaruthers, Marvin H.
dc.date.accessioned2018-05-15T20:13:12Z
dc.date.available2018-05-15T20:13:12Z
dc.date.issued2000-02
dc.identifier.citationBeaucage, Serge L.; Caruthers, Marvin H. (2000). "Synthetic Strategies and Parameters Involved in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method." Current Protocols in Nucleic Acid Chemistry 00(1): 3.3.1-3.3.20.
dc.identifier.issn1934-9270
dc.identifier.issn1934-9289
dc.identifier.urihttps://hdl.handle.net/2027.42/143633
dc.description.abstractThe phosphoramidite approach has had a major impact on the synthesis of oligonucleotides. This unit describes parameters that affect the performance of this method for preparing oligodeoxyribonucleotides, as well as a number of compatible strategies. Milestones that led to the discovery of the approach are chronologically reported. Alternate strategies are also described to underscore the versatility by which these synthons can be obtained. Mechanisms of deoxyribonucleoside phosphoramidite activation, factors affecting condensation, and deprotection strategies are discussed.
dc.publisherWiley Periodicals, Inc.
dc.publisherPlenum
dc.titleSynthetic Strategies and Parameters Involved in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method
dc.typeArticleen_US
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemical Engineering
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbsecondlevelPublic Health
dc.subject.hlbsecondlevelBiological Chemistry
dc.subject.hlbtoplevelEngineering
dc.subject.hlbtoplevelHealth Sciences
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttps://deepblue.lib.umich.edu/bitstream/2027.42/143633/1/cpnc0303.pdf
dc.identifier.doi10.1002/0471142700.nc0303s00
dc.identifier.sourceCurrent Protocols in Nucleic Acid Chemistry
dc.identifier.citedreferenceStec, W.J., Uznanski, B., Wilk, A., Hirschbein, B.L., Fearon, K.L., and Bergot, B.J. 1993. Bis( O,O ‐diisopropoxy phosphinothioyl) disulfide—A highly efficient sulfurizing reagent for cost‐effective synthesis of oligo(nucleoside phosphorothioate)s. Tetrahedron Lett. 34: 5317 ‐ 5320.
dc.identifier.citedreferenceUznanski, B., Grajkowski, A., and Wilk, A. 1989. The isopropoxyacetic group for convenient base protection during solid‐support synthesis of oligodeoxyribonucleotides and their triester analogs. Nucl. Acids Res. 17: 4863 ‐ 4871.
dc.identifier.citedreferenceVargeese, C., Carter, J., Yegge, J., Krivjansky, S., Settle, A., Kropp, E., Peterson, K., and Pieken, W. 1998. Efficient activation of nucleoside phosphoramidites with 4,5‐dicyanoimidazole during oligonucleotide synthesis. Nucl. Acids Res. 26: 1046 ‐ 1050.
dc.identifier.citedreferenceVirnekäs, B., Ge, L., Plückthun, A., Schneider, K.C., Wellnhofer, G., and Moroney, S.E. 1994. Trinucleotide phosphoramidites: ideal reagents for the synthesis of mixed oligonucleotides for random mutagenesis. Nucl. Acids Res. 22: 5600 ‐ 5607.
dc.identifier.citedreferenceVu, H. and Hirschbein, B.L. 1991. Internucleotide phosphite sulfurization with tetraethylthiuram disulfide. Phosphorothioate oligonucleotide synthesis via phosphoramidite chemistry. Tetrahedron Lett. 32: 3005 ‐ 3008.
dc.identifier.citedreferenceVu, H., McCollum, C., Jacobson, K., Theisen, P., Vinayak, R., Spiess, E., and Andrus, A. 1990. Fast oligonucleotide deprotection phosphoramidite chemistry for DNA synthesis. Tetrahedron Lett. 31: 7269 ‐ 7272.
dc.identifier.citedreferenceWeber, H. and Khorana, H.G. 1972. CIV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxynucleotide corresponding to the nucleotide sequence 21 to 40. J. Mol. Biol. 72: 219 ‐ 249.
dc.identifier.citedreferenceWeiss, P. 1998. TOM‐protecting group—A major improvement in RNA synthesis. The Glen Report 11: 2 ‐ 4.
dc.identifier.citedreferenceWilk, A., Srinivasachar, K., and Beaucage, S.L. 1997. N ‐Trifluoroacetylamino alcohols as phosphodiester protecting groups in the synthesis of oligodeoxyribonucleotides. J. Org. Chem. 62: 6712 ‐ 6713.
dc.identifier.citedreferenceWincott, F., DiRenzo, A., Shaffer, C., Grimm, S., Tracz, D., Workman, C., Sweedler, D., Gonzalez, C., Scaringe, S., and Usman, N. 1995. Synthesis, deprotection, analysis and purification of RNA and ribosymes. Nucl. Acids Res. 23: 2677 ‐ 2684.
dc.identifier.citedreferenceWolter, A., Biernat, J., and Köster, H. 1986. Polymer support oligonucleotide synthesis XX: Synthesis of a henhectacosa deoxynucleotide by use of a dimeric phosphoramidite synthon. Nucleosides Nucleotides 5: 65 ‐ 77.
dc.identifier.citedreferenceWu, X. and Pitsch, S. 1998. Synthesis and pairing properties of oligoribonucleotide analogues containing a metal‐binding site attached to β‐D‐allofuranosyl cytosine. Nucl. Acids Res. 26: 4315 ‐ 4323.
dc.identifier.citedreferenceXin, Z. and Just, G. 1996. Diastereoselective synthesis of phosphite triesters. Tetrahedron Lett. 37: 969 ‐ 972.
dc.identifier.citedreferenceXu, Q., Barany, G., Hammer, R.P., Musier‐Forsyth, K. 1996. Efficient introduction of phosphorothioates into RNA oligonucleotides by 3‐ethoxy‐1,2,4‐dithiazoline‐5‐one (EDITH). Nucl. Acids Res. 24: 3643 ‐ 3644.
dc.identifier.citedreferenceYamana, K., Nishijima, Y., Oka, A., Nakano, H., Sangen, O., Ozaki, H., and Shimidzu, T. 1989. A simple preparation of 5′‐ O ‐dimethoxytrityl deoxyribonucleoside 3′‐ O ‐phosphor‐bisdiethylamidites as useful intermediates in the synthesis of oligodeoxyribonucleotides and their phosphorodiethylamidate analogs on a solid support. Tetrahedron 45: 4135 ‐ 4140.
dc.identifier.citedreferenceYu, D., Tang, J.‐Y., Iyer, R.P., and Agrawal, S. 1994. Diethoxy N,N ‐diisopropyl phosphoramidite as an improved capping reagent in the synthesis of oligonucleotides using phosphoramidite chemistry. Tetrahedron Lett. 35: 8565 ‐ 8568.
dc.identifier.citedreferenceZehl, A., Starke, A., Cech, D., Hartsch, T., Merkl, R., and Fritz, H.‐J. 1996. Efficient and flexible access to fully protected trinucleotides suitable for DNA synthesis by automated phosphoramidite chemistry. Chem. Commun. 2677 ‐ 2678.
dc.identifier.citedreferenceZemlicka, J. and Holy, A. 1967. Preparation of N ‐dimethylaminomethylene derivatives—A new method of a selective substitution of nucleoside amino groups. Coll. Czech. Chem. Commun. 32: 3159 ‐ 3168.
dc.identifier.citedreferenceZhang, Z., Nichols, A., Alsbeti, M., Tang, J.X., and Tang, J.Y. 1998. Solid phase synthesis of oligonucleotide phosphorothioate analogues using bis(ethoxythiocarbonyl)tetrasulfide as a new sulfur‐transfer reagent. Tetrahedron Lett. 39: 2467 ‐ 2470.
dc.identifier.citedreferenceZhang, Z., Nichols, A., Tang, J.X., Han, Y., and Tang, J.Y. 1999. Solid phase synthesis of oligonucleotide phosphorothioate analogues using 3‐methyl‐1,2,4‐dithiazolin‐5‐one (MEDITH) as a new sulfur‐transfer reagent. Tetrahedron Lett. 40: 2095 ‐ 2098.
dc.identifier.citedreferenceZhao, Z. and Caruthers, M.H. 1996. Synthesis and preliminary biochemical studies with 5′‐deoxy‐5′‐methylidyne phosphonate linked thymidine oligonucleotides. Tetrahedron Lett. 37: 6239 ‐ 6242.
dc.identifier.citedreferenceZon, G., Gallo, K.A., Samson, C.J., Shao, K., Summers, M.F., and Byrd, R.A. 1985. Analytical studies of ‘mixed sequence’ oligodeoxyribonucleotides synthesized by competitive coupling of either methyl‐ or β‐cyanoethyl‐ N, N ‐diisopropylamino phosphoramidite reagents, including 2′‐deoxyinosine. Nucl. Acids Res. 13: 8181 ‐ 8196.
dc.identifier.citedreferenceAdams, S.P., Kavka, K.S., Wykes, E.J., Holder, S.B., and Galluppi, G.R. 1983. Hindered dialkylamino nucleoside phosphite reagents in the synthesis of two DNA 51‐mers. J. Am. Chem. Soc. 105: 661 ‐ 663.
dc.identifier.citedreferenceAgrawal, S. and Iyer, R.P. 1995. Modified oligonucleotides as therapeutic and diagnostic agents. Curr. Opin. Biotechnol. 6: 12 ‐ 19.
dc.identifier.citedreferenceAndrus, A. and Beaucage, S.L. 1988. 2‐Mercaptobenzothiazole—An improved reagent for the removal of methyl phosphate protecting groups from oligodeoxynucleotide phosphotriesters. Tetrahedron Lett. 29: 5479 ‐ 5482.
dc.identifier.citedreferenceAnonymous. 1996. Non‐aqueous oxidation with 10‐camphorsulfonyl‐oxaziridine. The Glen Report 9: 8 ‐ 9.
dc.identifier.citedreferenceArnold, L., Tocik, Z., Bradkova, E., Hostomsky, Z., Paces, V., and Smrt, J. 1989. Automated chloridite and amidite synthesis of oligodeoxyribonucleotides on a long chain support using amidine protected purine nucleosides. Collect. Czech. Chem. Commun. 54: 523 ‐ 532.
dc.identifier.citedreferenceArterburn, J.B. and Perry, M.C. 1997. Rhenium catalyzed sulfurization of phosphorus(III) compounds with thiiranes: New reagents for phosphorothioate ester synthesis. Tetrahedron Lett. 38: 7701 ‐ 7704.
dc.identifier.citedreferenceBarone, A.D., Tang, J.‐Y., and Caruthers, M.H. 1984. In situ activation of bis‐dialkylaminophosphines—A new method for synthesizing deoxyoligonucleotides on polymer supports. Nucl. Acids Res. 12: 4051 ‐ 4061.
dc.identifier.citedreferenceBeaucage, S.L. 1984. A simple and efficient preparation of deoxynucleoside phosphoramidites in situ. Tetrahedron Lett. 25: 375 ‐ 378.
dc.identifier.citedreferenceBeaucage, S.L. and Caruthers, M.H. 1981. Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis. Tetrahedron Lett. 22: 1859 ‐ 1862.
dc.identifier.citedreferenceBeaucage, S.L. and Iyer, R.P. 1992. Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron 48: 2223 ‐ 2311.
dc.identifier.citedreferenceBeaucage, S.L. and Iyer, R.P. 1993. The synthesis of modified oligonucleotides by the phosphoramidite approach and their applications. Tetrahedron 49: 6123 ‐ 6194.
dc.identifier.citedreferenceBeier, M. and Pfleiderer, W. 1999. Pyridinium salts–An effective class of catalysts for oligonucleotide synthesis. Helv. Chim. Acta 82: 879 ‐ 887.
dc.identifier.citedreferenceBentrude, W.G., Sopchik, A.E., and Gajda, T. 1989. Stereo‐ and regiochemistries of the oxidations of 2‐methoxy‐5‐ tert ‐butyl‐1,3,2‐dioxaphosphorinanes and the cyclic methyl 3′,5′‐phosphite of thymidine by H 2 O/I 2 and O 2 /AIBN to P‐chiral phosphates. 17 O NMR assignment of phosphorus configuration to the diastereomeric thymidine cyclic methyl 3′,5′‐monophosphates. J. Am. Chem. Soc. 111: 3981 ‐ 3987.
dc.identifier.citedreferenceBergstrom, D.E. and Gerry, N. 1994. Precision sequence‐specific cleavage of a nucleic acid by a minor‐groove‐directed metal‐binding ligand linked through N‐2 of deoxyguanosine. J. Am. Chem. Soc. 116: 12067 ‐ 12068.
dc.identifier.citedreferenceBerner, S., Mühlegger, K., and Seliger, H. 1989. Studies on the role of tetrazole in the activation of phosphoramidites. Nucl. Acids Res. 17: 853 ‐ 864.
dc.identifier.citedreferenceBoal, J.H., Wilk, A., Harindranath, N., Max, E.E., Kempe, T., and Beaucage, S.L. 1996. Cleavage of oligodeoxyribonucleotides from controlled‐pore glass supports and their rapid deprotection by gaseous amines. Nucl. Acids Res. 24: 3115 ‐ 3117.
dc.identifier.citedreferenceBoudjebel, H., Goncçalves, H., and Mathis, F. 1975. Étude de la liaison P—N dans le motif S 2 P—NMe 3 en résonance magnétique nucléaire et par la réaction d’échange avec le trifluoroacétate de méthyle. Bull. Chem. Soc. Chim. France 628 ‐ 634.
dc.identifier.citedreferenceBrill, W.K.‐D., Nielsen, J., and Caruthers, M.H. 1991. Synthesis of deoxydinucleoside phosphorodithioates. J. Am. Chem. Soc. 113: 3972 ‐ 3980.
dc.identifier.citedreferenceCaruthers, M.H., Beaucage, S.L., Becker, C., Efcavitch, W., Fisher, E.F., Galluppi, G., Goldman, R., deHaseth, P., Martin, F., Matteucci, M., and Stabinsky, Y. 1982. New methods for synthesizing deoxyoligonucleotides. In Genetic Engineering: Principles and Methods, Vol. 4 ( J.K. Setlow and A. Hollaender, eds.) pp. 1 ‐ 17. Plenum, New York.
dc.identifier.citedreferenceCaruthers, M.H., Barone, A.D., Beaucage, S.L., Dodds, D.R., Fisher, E.F., McBride, L.J., Matteucci, M., Stabinsky, Z., and Tang, Y.‐Y. 1987a. Chemical synthesis of deoxyoligonucleotides by the phosphoramidite method. In Methods and Enzymology; Vol. 154 ( R. Wu and L. Grossman, eds.) pp. 287 ‐ 313. Academic Press, San Diego; and references therein.
dc.identifier.citedreferenceCaruthers, M.H., Kierzek, R., and Tang, J.Y. 1987b. Synthesis of oligonucleotides using the phosphoramidite method. In Biophosphates and Their Analogues—Synthesis, Structure, Metabolism and Activity ( K.S. Bruzik and W.J. Stec, eds.) pp. 3 ‐ 21. Elsevier/North Holland, Amsterdam.
dc.identifier.citedreferenceCasale, R. and McLaughlin, L.W. 1990. Synthesis and properties of an oligodeoxynucleotide containing a polycyclic aromatic hydrocarbon site specifically bound to the N 2 amino group of a 2′‐deoxyguanosine residue. J. Am. Chem. Soc. 112: 5264 ‐ 5271.
dc.identifier.citedreferenceClaesen, C., Tesser, G.I., Dreef, C.E., Marugg, J.E., van der Marel, G.A., and van Boom, J.H. 1984. Use of 2‐methylsulfonylethyl as a phosphorus protecting group in oligonucleotide synthesis via a phosphite triester approach. Tetrahedron Lett. 25: 1307 ‐ 1310.
dc.identifier.citedreferenceCrooke, S.T. and Bennett, C.F. 1996. Progress in antisense oligonucleotide therapeutics. Annu. Rev. Pharmacol. Toxicol. 36: 107 ‐ 129.
dc.identifier.citedreferenceDahl, B.H., Nielsen, J., and Dahl, O. 1987. Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nucleophilic catalysis by tetrazole and rate variations with the phosphorus substituents. Nucl. Acids Res. 15: 1729 ‐ 1743.
dc.identifier.citedreferenceDahl, B.H., Bjergårde, K., Henriksen, L., and Dahl, O. 1990. A highly reactive, odourless substitute for thiophenol/triethylamine as a deprotection reagent in the synthesis of oligonucleotides and their analogues. Acta Chem. Scand. 44: 639 ‐ 641.
dc.identifier.citedreferenceDaub, G.W. and van Tamelen, E.E. 1977. Synthesis of oligoribonucleotides based on the facile cleavage of methyl phosphotriester intermediates. J. Am. Chem. Soc. 99: 3526 ‐ 3528.
dc.identifier.citedreferencedeBear, J.S., Hayes, J.A., Koleck, M.P., and Gough, G.R. 1987. A universal glass support for oligonucleotide synthesis. Nucleosides Nucleotides 6: 821 ‐ 830.
dc.identifier.citedreferenceEadie, J.S. and Davidson, D.S. 1987. Guanine modification during chemical DNA synthesis. Nucl. Acids Res. 15: 8333 ‐ 8349.
dc.identifier.citedreferenceEckstein, F. 1985. Nucleoside phosphorothioates. Annu. Rev. Biochem. 54: 367 ‐ 402.
dc.identifier.citedreferenceEfimov, V.A., Kalinkina, A.L., Chakhmakhcheva, O.G., Schmaltz Hill, T., and Jayaraman, K. 1995. New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues. Nucl. Acids Res. 23: 4029 ‐ 4033.
dc.identifier.citedreferenceFarrance, I.K., Eadie, J.S., and Ivarie, R. 1989. Improved chemistry for oligodeoxyribonucleotide synthesis substantially improves restriction enzyme cleavage of a synthetic 35 mer. Nucl. Acids Res. 17: 1231 ‐ 1245.
dc.identifier.citedreferenceFourrey, J.‐L. and Varenne, J. 1984. Improved procedure for the preparation of deoxynucleoside phosphoramidites: Arylphosphoramidites as new convenient intermediates for oligodeoxynucleotide synthesis. Tetrahedron Lett. 25: 4511 ‐ 4514.
dc.identifier.citedreferenceFourrey, J.‐L. and Varenne, J. 1985. Introduction of a nonaqueous oxidation procedure in the phosphite triester route for oligonucleotide synthesis. Tetrahedron Lett. 26: 1217 ‐ 1220.
dc.identifier.citedreferenceFourrey, J.‐L., Varenne, J., Fontaine, C., Guittet, E., and Yang, Z.W. 1987. A new method for the synthesis of branched ribonucleotides. Tetrahedron Lett. 28: 1769 ‐ 1772.
dc.identifier.citedreferenceFroehler, B. and Matteucci, M.D. 1983. Substituted 5‐phenyltetrazoles: Improved activators of deoxynucleoside phosphoramidites in deoxyoligonucleotide synthesis. Tetrahedron Lett. 24: 3171 ‐ 3174.
dc.identifier.citedreferenceGaytán, P., Yañez, J., Sánchez, F., Mackie, H., and Soberón, X. 1998. Combination of DMT‐mononucleotide and Fmoc‐trinucleotide phosphoramidites in oligonucleotide synthesis affords an automatable codon‐level mutagenesis method. Chem. Biol. 5: 519 ‐ 527.
dc.identifier.citedreferenceGryaznov, S.M. and Letsinger, R.L. 1991. Synthesis of oligonucleotides via monomers with unprotected bases. J. Am. Chem. Soc. 113: 5876 ‐ 5877.
dc.identifier.citedreferenceGryaznov, S.M. and Letsinger, R.L. 1992. Selective O‐phosphitilation with nucleoside phosphoramidite reagents. Nucl. Acids Res. 20: 1879 ‐ 1882.
dc.identifier.citedreferenceGuo, M., Yu, D., Iyer, R.P., and Agrawal, S. 1998. Solid‐phase stereoselective synthesis of 2′‐ O ‐methyl oligoribonucleoside phosphorothioates using nucleoside oxazaphospholidines. Bioorg. Med. Chem. Lett. 8: 2539 ‐ 2544.
dc.identifier.citedreferenceHayakawa, Y. and Kataoka, M. 1998. Facile synthesis of oligodeoxyribonucleotides via the phosphoramidite method without nucleoside base protection. J. Am. Chem. Soc. 120: 12395 ‐ 12401.
dc.identifier.citedreferenceHayakawa, Y., Uchiyama, M., and Noyori, R. 1986. Nonaqueous oxidation of nucleoside phosphites to the phosphates. Tetrahedron Lett. 27: 4191 ‐ 4194.
dc.identifier.citedreferenceHayakawa, Y., Kataoka, M., and Noyori, R. 1996. Benzimidazolium triflate as an efficient promoter for nucleotide synthesis via the phosphoramidite method. J. Org. Chem. 61: 7996 ‐ 7997.
dc.identifier.citedreferenceHering, G., Stöcklein‐Schneiderwind, R., Ugi, I., Pathak, T., Balgobin, N., and Chattopadhyaya, J. 1985. Preparation and properties of chloro‐N,N‐dialkylamino‐2,2,2‐trichloroethoxy‐ and chloro‐N,N‐dialkylamino‐2,2,2‐trichloro‐1,1‐ dimethylethoxyphosphines and their deoxynucleoside phosphiteamidates. Nucleosides Nucleotides 4: 169 ‐ 171.
dc.identifier.citedreferenceIyer, R.P., Phillips, L.R., Egan, W., Regan, J.B., and Beaucage, S.L. 1990. The automated synthesis of sulfur‐containing oligodeoxyribonucleotides using 3 H ‐1,2‐benzodithiol‐3‐one 1,1‐dioxide as a sulfur‐transfer reagent. J. Org. Chem. 55: 4693 ‐ 4698.
dc.identifier.citedreferenceIyer, R.P., Yu, D., Habus, I., Ho, N.‐H., Johnson, S., Devlin, T., Jiang, Z., Zhou, W., Xie, J., and Agrawal, S. 1997. N ‐Pent‐4‐enoyl (PNT) group as a universal nucleobase protector: Applications in the rapid and facile synthesis of oligonucleotides, analogs, and conjugates. Tetrahedron 53: 2731 ‐ 2750.
dc.identifier.citedreferenceIyer, R.P., Guo, M.‐J., Yu, D., and Agrawal, S. 1998. Solid‐phase stereoselective synthesis of oligonucleoside phosphorothioates: The nucleoside bicyclic oxazaphospholidines as novel synthons. Tetrahedron Lett. 39: 2491 ‐ 2494.
dc.identifier.citedreferenceIyer, R.P., Roland, A., Zhou, W., and Ghosh, K. 1999. Modified oligonucleotides—Synthesis, properties and applications. Curr. Opin. Mol. Ther. 1: 344 ‐ 358.
dc.identifier.citedreferenceJørgensen, P.N., Stein, P.C., and Wengel, J. 1994. Synthesis of 3′‐ C ‐(hydroxymethyl) thymidine: Introduction of a novel class of dexoynucleosides and oligodeoxynucleotides. J. Am. Chem. Soc. 116: 2231 ‐ 2232.
dc.identifier.citedreferenceJosephson, S., Lagerholm, E., and Palm, G. 1984. Automatic synthesis of oligodeoxynucleotides and mixed oligodeoxynucleotides using the phosphoramidite method. Acta Chem. Scand. B38: 539 ‐ 545.
dc.identifier.citedreferenceKamer, P.C.J., Roelen, H.C.P.F., van den Elst, H., van der Marel, G.A., and van Boom, J.H. 1989. An efficient approach toward the synthesis of phosphorothioate diesters via the Schönberg reaction. Tetrahedron Lett. 30: 6757 ‐ 6760.
dc.identifier.citedreferenceKayushin, A.L., Korosteleva, M.D., Miroshnikov, A.I., Kosch, W., Zubov, D., and Piel, N. 1996. A convenient approach to the synthesis of trinucleotide phosphoramidites—Synthons for the generation of oligonucleotide/peptide libraries. Nucl. Acids Res. 24: 3748 ‐ 3755.
dc.identifier.citedreferenceKhorana, H.G. 1968. Nucleic acid synthesis. Pure Appl. Chem. 17: 349 ‐ 381.
dc.identifier.citedreferenceKierzek, R., Rozek, M., and Markiewicz, W.T. 1987. Some steric aspects of synthesis of oligoribonucleotides by phosphoramidite approach on solid support. Nucl. Acids Res. Symp. Ser. No. 18: 201 ‐ 204.
dc.identifier.citedreferenceKofoed, T. and Caruthers, M.H. 1996. Synthesis of 5′‐phosphonate linked thymidine deoxyoligonucleotides. Tetrahedron Lett. 37: 6457 ‐ 6460.
dc.identifier.citedreferenceKrotz, A.H., Klopchin, P.G., Walker, K.L., Srivatsa, G.S., Cole, D.L., and Ravikumar, V.T. 1997a. On the formation of longmers in phosphorothioate oligodeoxyribonucleotide synthesis. Tetrahedron Lett. 38: 3875 ‐ 3878.
dc.identifier.citedreferenceKrotz, A.H., Klopchin, P., Cole, D.L., and Ravikumar, V.T. 1997b. Improved purity profile of phosphorothioate oligonucleotides through the use of dimeric phosphoramidite synthons. Nucleosides Nucleotides 16: 1637 ‐ 1640.
dc.identifier.citedreferenceKuijpers, W.H.A., Huskens, J., and van Boeckel, C.A.A. 1990. The 2‐(acetoxymethyl)benzoyl (AMB) group as a new base‐protecting group, designed for the protection of (phosphate) modified oligonucleotides. Tetrahedron Lett. 31: 6729 ‐ 6732.
dc.identifier.citedreferenceKumar, G. and Poonian, M.S. 1984. Improvements in oligodeoxyribonucleotide synthesis: Methyl N, N ‐dialkylphosphoramidite dimer units for solid support phosphite methodology. J. Org. Chem. 49: 4905 ‐ 4912.
dc.identifier.citedreferenceLee, H.‐J. and Moon, S.‐H. 1984. Bis‐( N,N ‐dialkylamino)‐alkoxyphosphines as a new class of phosphite coupling agent for the synthesis of oligonucleotides. Chem. Lett. 1229 ‐ 1232.
dc.identifier.citedreferenceLetsinger, R.L. and Lunsford, W.B. 1976. Synthesis of thymidine oligonucleotides by phosphite triester intermediates. J. Am. Chem. Soc. 98: 3655 ‐ 3661.
dc.identifier.citedreferenceLetsinger, R.L. and Mahadevan, V. 1966. Stepwise synthesis of oligodeoxyribonucleotides on an insoluble polymer support. J. Am. Chem. Soc. 88: 5319 ‐ 5324.
dc.identifier.citedreferenceLetsinger, R.L. and Ogilvie, K.K. 1969. Synthesis of oligothymidylates via phosphotriester intermediates. J. Am. Chem. Soc. 91: 3350 ‐ 3355.
dc.identifier.citedreferenceLyttle, M.H., Napolitano, E.W., Calio, B.L., and Kauvar, L.M. 1995. Mutagenesis using trinucleotide β‐cyanoethyl phosphoramidites. BioTechniques 19: 274 ‐ 280.
dc.identifier.citedreferenceMathis, R., Lafaille, L., and Burgada, R. 1974. Fréquence d’absorption de la liaison P‐N dans des composés du phosphore tricoordonné. Spectrochim. Acta, Part A 30: 357 ‐ 370.
dc.identifier.citedreferenceMatteucci, M.D. and Caruthers, M.H. 1981. Synthesis of deoxyoligonucleotides on a polymer support. J. Am. Chem. Soc. 103: 3185 ‐ 3191.
dc.identifier.citedreferenceMcBride, L.J. and Caruthers, M.H. 1983. An investigation of several deoxynucleoside phosphoramidites useful for synthesizing deoxyoligonucleotides. Tetrahedron Lett. 24: 245 ‐ 248.
dc.identifier.citedreferenceMcBride, L.J., Kierzek, R., Beaucage, S.L., and Caruthers, M.H. 1986. Amidine protecting groups for oligonucleotide synthesis. J. Am. Chem. Soc. 108: 2040 ‐ 2048.
dc.identifier.citedreferenceMontserrat, F.X., Cerandas, A., Eritja, R., and Pedroso, E. 1994. Criteria for the economic large scale solid‐phase synthesis of oligonucleotides. Tetrahedron 50: 2617 ‐ 2622.
dc.identifier.citedreferenceMoore, M.F. and Beaucage, S.L. 1985. Conceptual basis of the selective activation of bis(dialkylamino)methoxyphosphines by weak acids and its application toward the preparation of deoxynucleoside phosphoramidites in situ. J. Org. Chem. 50: 2019 ‐ 2025.
dc.identifier.citedreferenceMullah, B., Andrus, A., Zhao, H., and Jones, R.A. 1995. Oxidative conversion of N ‐dimethylformamidine nucleosides to N ‐cyano nucleosides. Tetrahedron Lett. 36: 4373 ‐ 4376.
dc.identifier.citedreferenceNatt, F. and Häner, R. 1997. Lipocap: A lipophilic phosphoramidite‐based capping reagent. Tetrahedron 53: 9629 ‐ 9636.
dc.identifier.citedreferenceNeuner, P., Cortese, R., and Monaci, P. 1998. Codon‐based mutagenesis using dimer‐phosphoramidites. Nucl. Acids Res. 26: 1223 ‐ 1227.
dc.identifier.citedreferenceNielsen, J. and Caruthers, M.H. 1988. Directed Arbuzov‐type reactions of 2‐cyano‐1,1‐dimethylethyl deoxynucleoside phosphites. J. Am. Chem. Soc. 110: 6275 ‐ 6276.
dc.identifier.citedreferenceOno, A., Matsuda, A., Zhao, J., and Santi, D.V. 1995. The synthesis of blocked triplet‐phosphoramidites and their use in mutagenesis. Nucl. Acids Res. 23: 4677 ‐ 4682.
dc.identifier.citedreferencePolushin, N.N. 1996. Synthesis of functionally modified oligonucleotides from methoxyoxalamido precursors. Tetrahedron Lett. 37: 3231 ‐ 3234.
dc.identifier.citedreferencePon, R.T., Usman, N., Damha, M.J., and Ogilvie, K.K. 1986. Prevention of guanine modification and chain cleavage during the solid phase synthesis of oligonucleotides using phosphoramidite derivatives. Nucl. Acids Res. 14: 6453 ‐ 6470.
dc.identifier.citedreferencePon, R.T. 1987. Enhanced coupling efficiency using 4‐dimethylamino pyridine (DMAP) and either tetrazole, 5‐( o ‐nitrophenyl) tetrazole or 5‐( p ‐nitrophenyl) tetrazole in the solid phase synthesis of oligoribonucleotides by the phosphoramidite procedure. Tetrahedron Lett. 28: 3643 ‐ 3646.
dc.identifier.citedreferenceRao, M.V. and Macfarlane, K. 1994. Solid phase synthesis of phosphorothioate oligonucleotides using benzyltriethylammonium tetrathiomolybdate as a rapid sulfur transfer reagent. Tetrahedron Lett. 35: 6741 ‐ 6744.
dc.identifier.citedreferenceRao, M.V., Reese, C.B., and Zhengyun, Z. 1992. Dibenzoyl tetrasulphide—A rapid sulphur transfer agent in the synthesis of phosphorothioate analogues of oligonucleotides. Tetrahedron Lett. 33: 4839 ‐ 4842.
dc.identifier.citedreferenceReddy, M.P., Hanna, N.B., and Farooqui, F. 1994. Fast cleavage and deprotection of oligonucleotides. Tetrahedron Lett. 35: 4311 ‐ 4314.
dc.identifier.citedreferenceReddy, M.P., Hanna, N.B., and Farooqui, F. 1997. Ultrafast cleavage and deprotection of oligonucleotides—Synthesis and use of C Ac derivatives. Nucleosides Nucleotides 16: 1589 ‐ 1598.
dc.identifier.citedreferenceRegan, J.B., Phillips, L.R., and Beaucage, S.L. 1992. Large‐scale preparation of the sulfur‐transfer reagent 3 H ‐1,2‐benzodithiol‐3‐one 1,1‐dioxide. Org. Prep. Proc. Int. 24: 488 ‐ 492.
dc.identifier.citedreferenceRoelen, H.C.P.F., Kamer, P.C.J., van den Elst, H., van der Marel, G.A., and van Boom, J.H. 1991. A study on the use of phenylacetyl disulfide in the solid‐phase synthesis of oligodeoxynucleoside phosphorothioates. Recl. Trav. Chim. Pays‐Bas 110: 325 ‐ 331.
dc.identifier.citedreferenceSanghvi, Y.S. and Cook, P.D. 1994. Carbohydrates: Synthetic methods and applications in antisense therapeutics. In ACS Symposium Series 580—Carbohydrate Modifications in Antisense Research ( Y.S. Sanghvi and P.D. Cook, eds.) pp. 1 ‐ 22. American Chemical Society, Washington, D.C.
dc.identifier.citedreferenceSchulhof, J.C., Molko, D., and Teoule, R. 1987. The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base‐protecting groups. Nucl. Acids Res. 15: 397 ‐ 416.
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 ‐( o ‐nitrobenzyloxymethyl)‐protected monomers. Bioorg. Med. Chem. Lett. 2: 1019 ‐ 1024.
dc.identifier.citedreferenceSekine, M., Masuda, N., and Hata, T. 1986. Synthesis of oligodeoxyribonucleotides involving a rapid procedure for the removal of base‐protecting groups by use of the 4,4′,4″‐tris(benzoyloxy)trityl (TBTr) group. Bull. Chem. Soc. Jpn. 59: 1781 ‐ 1789.
dc.identifier.citedreferenceSeliger, H. and Gupta, K.C. 1985. Three‐phase synthesis of oligonucleotides. Angew. Chem. Int. Ed. Engl. 24: 685 ‐ 687.
dc.identifier.citedreferenceSinha, N.D., Biernat, J., McManus, J., and Köster, H. 1984. Polymer support oligonucleotide synthesis XVIII: Use of β‐cyanoethyl‐ N,N ‐dialkyl‐amino‐/ N ‐morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucl. Acids Res. 12: 4539 ‐ 4557.
dc.identifier.citedreferenceSinha, N.D., Davis, P., Usman, N., Pérez, J., Hodge, R., Kremsky, J., and Casale, R. 1993. Labile exocyclic amine protection of nucleosides in DNA, RNA and oligonucleotide analog synthesis facilitating N ‐deacylation, minimizing depurination and chain degradation. Biochimie 75: 13 ‐ 23.
dc.identifier.citedreferenceSondek, J. and Shortle, D. 1992. A general strategy for random insertion and substitution mutagenesis: Substoichiometric coupling of trinucleotide phosphoramidites. Proc. Natl. Acad. Sci. U.S.A. 89: 3581 ‐ 3585.
dc.identifier.citedreferenceStec, W.J. and Zon, G. 1984. Stereochemical studies of the formation of chiral internucleotide linkages by phosphoramidite coupling in the synthesis of oligodeoxyribonucleotides. Tetrahedron Lett. 25: 5279 ‐ 5282.
dc.identifier.citedreferenceTanaka, T. and Letsinger, R.L. 1982. Syringe method for the stepwise chemical synthesis of oligonucleotides. Nucl. Acids Res. 10: 3249 ‐ 3260.
dc.identifier.citedreferenceTener, G.M. 1961. 2‐Cyanoethyl phosphate and its use in the synthesis of phosphate esters. J. Am. Chem. Soc. 83: 159 ‐ 168.
dc.identifier.citedreferenceUgi, I., Jacob, P., Landgraf, B., Rupp, C., Lemmen, P., and Verfïrth, U. 1988. Phosphite oxidation and the preparation of five‐membered cyclic phosphorylating reagents via the phosphites. Nucleosides Nucleotides 7: 605 ‐ 608.
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


Files in this item

Show simple item record

Remediation of Harmful Language

The University of Michigan Library aims to describe library materials in a way that respects the people and communities who create, use, and are represented in our collections. Report harmful or offensive language in catalog records, finding aids, or elsewhere in our collections anonymously through our metadata feedback form. More information at Remediation of Harmful Language.

Accessibility

If you are unable to use this file in its current format, please select the Contact Us link and we can modify it to make it more accessible to you.