Synthese von Oligodesoxynucleotiden über Phosphorsäuretriester
Abstract
Eine neue Methode zur Synthese von Oligodesoxynucleotiden wird untersucht, bei der die Internucleotid‐Phosphorsäuregruppe mit dem durch Zink abspaltbaren Trichloräthylrest verestert ist. Auf diese Weise werden d(TpT, d(TpTpT), d(TpTpTpT), d(CpT), d(ApT), d(ApA) und d(ApApA) synthetisiert. Mit Hilfe der kernmagnetischen Resonanz wird wahrscheinlich gemacht, daß durch Aktivierung von Nucleosid‐3′‐phosphorsäure‐trichloräthylestern mit 2.4.6‐Triisopropyl‐benzolsulfonylchlorid ein Pyrophosphorsäure‐tetraester (18) gebildet wird, der mit der 5′‐OH‐Gruppe eines Nucleosids zu dem Dinucleosidphosphorsäure‐trichloräthylester reagiert.
Number of times cited: 46
- P.R. Hanson, N. Asad, Q. Zang, S. Jayashinghe and J. Markley, 6.12 Inorganic Acid Derivatives, Comprehensive Organic Synthesis II, 10.1016/B978-0-08-097742-3.00618-2, (479-554), (2014).
- Dmitry A. Stetsenko, Oligonucleotides and their Derivatives, The Power of Functional Resins in Organic Synthesis, (529-583), (2009).
- Saran A. Narang, Wing L. Sung and Robert H. Wightman, Gene Synthesis, Total Synthesis of Natural Products, (51-84), (2007).
- Colin B. Reese, Oligo- and poly-nucleotides: 50 years of chemical synthesis, Organic & Biomolecular Chemistry, 10.1039/b510458k, 3, 21, (3851), (2005).
- Günter Von Kiedrowski, 50 Jahre DNA‐Doppelhelix und Miller‐Experiment, Nachrichten aus der Chemie, 51, 6, (666-674), (2010).
- Colin B. Reese, The chemical synthesis of oligo- and poly-nucleotides: a personal commentary, Tetrahedron, 10.1016/S0040-4020(02)01084-0, 58, 44, (8893-8920), (2002).
- Yoshihiro Hayakawa, Toward an Ideal Synthesis of Oligonucleotides: Development of a Novel Phosphoramidite Method with High Capability, Bulletin of the Chemical Society of Japan, 74, 9, (1547), (2001).
- Isabel Mathieu‐Pelta and Slayton A. Evans, Bis(2,2,2‐trichloro‐1,1‐dimethylethyl) Phosphorochloridate, Encyclopedia of Reagents for Organic Synthesis, (2001).
- Karl-Heinz Metten, Kurt Hobert, Susanne Marzian, Ulrich E. Hackler, Uwe Heinz, Peter Welzel, Werner Aretz, Dirk Böttger, Udo Hedtmann, Gerhard Seibert, Astrid Markus, Michael Limbert, Yveline Van Heijenoort and Jean Van Heijenoort, The first enzymatic degradation products of the antibiotic moenomycin A., Tetrahedron, 48, 39, (8401), (1992).
- Yoshihiro Hayakawa, Inorganic Acid Derivatives, Comprehensive Organic Synthesis, 10.1016/B978-0-08-052349-1.00167-0, (601-630), (1991).
- J. Tomasz, S. Bottka and I. Pelozer, A31P NMR Study of the Reaction of Adenosine 3′ 5′-Cyclic Monophosphate with 2, 4, 6-Triisopropylbenzenesulfonyl Chloride, Nucleosides and Nucleotides, 6, 4, (785), (1987).
- Suzanna J. Horvath, Joseph R. Firca, Tim Hunkapiller, Michael W. Hunkapiller and Leroy Hood, [16] An automated DNA synthesizer employing deoxynucleoside 3′-phosphoramidites, Recombinant DNA Part E, 10.1016/0076-6879(87)54082-4, (314-326), (1987).
- Hiroshi Seki and Oyo Mitsunobu, Formation of Interribonucleoside Phosphate Bond by the Use of Reagent Formed by the Reaction of 2-Chlorophenyl Phosphorodichloridate with 5-Nitrobenzotriazole and Preparation of Anticodon Triplet of Yeast tRNALys, Chemistry Letters, 16, 5, (775), (1987).
- E. Sonveaux, The organic chemistry underlying DNA synthesis, Bioorganic Chemistry, 14, 3, (274), (1986).
- Yu Wang, A total synthesis of yeast alanine transfer RNA, Accounts of Chemical Research, 17, 11, (393), (1984).
- Saran A. Narang, Chemical synthesis, cloning and expression of human preproinsulin gene, Journal of Biosciences, 6, 5, (739), (1984).
- C. A. A. van Boeckel, J. P. G. Hermans, P. Westerduin, J. J. Oltvoort, G. A. van der Marel and J. H. van Boom, Synthesis of two diphosphorylated lipid a derivatives containing α‐ or β‐anomeric phosphates, Recueil des Travaux Chimiques des Pays-Bas, 102, 10, (438-449), (2010).
- Saran A. Narang, DNA synthesis, Tetrahedron, 39, 1, (3), (1983).
- André Rosenthal , Dieter Cech and Zoe Alekseevna Šabarova, , Zeitschrift f�r Chemie, 23, 9, (317-327), (2010).
- J. Tomasz, 3′-3′,3′-5′ and 5′-5′ TpT-Amides: Synthesis, Characterization and Alkaline Hydrolysis, Nucleosides and Nucleotides, 2, 1, (51), (1983).
- Winfried Michels and Eckhard Schlimme, Darstellung und Konfigurationszuordnung der Diastereomeren des vollständig geschützten 2′‐Desoxyadenylyl‐(3′‐5′)‐2′‐desoxyadenosins, Liebigs Annalen der Chemie, 1982, 7, (1398-1402), (2006).
- Wojciech Dabkowski, Jan Michalski, Czeslaw Radziejewski and Zbigniew Skrzypczyński, Phosphoric and phosphinic sulfonic anhydrides – reinvestigation and corrections. Novel methods of synthesis, Chemische Berichte, 115, 4, (1636-1643), (2006).
- K.L. Sadana, F.E. Hruska and P.C. Loewen, A simplified strategy for the synthesis of dideoxyribonucleotide blocks, Tetrahedron Letters, 22, 35, (3367), (1981).
- Gunter Silber, Dieter Flockerzi, Rajendra Singh Varma, Ramamurthy Charubala, Eugen Uhlmann and Wolfgang Pfleiderer, , Helvetica Chimica Acta, 64, 5, (1704-1716), (2004).
- Eugen Uhlmann and Wolfgang Pfleiderer, , Helvetica Chimica Acta, 64, 5, (1688-1703), (2004).
- S.A. Narang, R. Brousseau, H.M. Hsiung and J.J. Michniewicz, [61] Chemical synthesis of deoxyoligonucleotides by the modified triester method, Nucleic Acids Part I, 10.1016/S0076-6879(80)65063-0, (610-620), (1980).
- D.G. Knorre and V.F. Zarytova, REACTIVE PHOSPHORYLATING INTERMEDIATES IN THE NUCLEIC ACIDS CHEMISTRY, Phosphorus Chemistry Directed Towards Biology, 10.1016/B978-0-08-023969-9.50007-X, (13-31), (1980).
- Ramamurthy Charubala and Wolfgang Pfleiderer, , Helvetica Chimica Acta, 62, 4, (1179-1193), (2004).
- Hiroshi Takaku, Masatoshi Yoshida, Masaatsu Kato and Tsujiaki Hata, 8-QUINOLINESULFONYL CHLORIDE: A NEW COUPLING AGENT IN OLIGORIBONUCLEOTIDE SYNTHESIS VIA PHOSPHOTRIESTER APPROACH, Chemistry Letters, 8, 7, (811), (1979).
- Morio Ikehara, Eiko Ohtsuka and Alexander F. Markham, The Synthesis of Polynucleotides, Advances in Carbohydrate Chemistry and Biochemistry Volume 36, 10.1016/S0065-2318(08)60236-X, (135-213), (1979).
- S.A. Narang, Hansen M. Hsiung and Roland Brousseau, [6] Improved phosphotriester method for the synthesis of gene fragments, Recombinant DNA, 10.1016/0076-6879(79)68008-4, (90-98), (1979).
- J.G. Lammers and J.H. van Boom, Synthesis of phospholipids via phosphotriester intermediates, Recueil des Travaux Chimiques des Pays-Bas, 98, 4, (243-250), (2010).
- Hiroshi Takaku, Ryuichi Yamaguchi, Tadaaki Nomoto and Tsujiaki Hata, 5-Chloro-8-quinolyl group as high efficient phosphate protecting group for the synthesis of oligoribonucleotides, Tetrahedron Letters, 20, 40, (3857), (1979).
- Ray Wu, Chander P. Bahl and Saran A. Narang, Synthetic Oligodeoxynucleotides for Analyses of DNA Structure and Function, , 10.1016/S0079-6603(08)60268-8, (101-141), (1978).
- J. H. van Boom and P. M. J. Burgers, The application of levulinic acid as protective group to the synthesis of tetradecaribonucleotide U‐A‐U‐A‐U‐A‐U‐A‐U‐A‐U‐A‐U‐A via the modified phosphotriester method, Recueil des Travaux Chimiques des Pays-Bas, 97, 3, (73-80), (2010).
- Colin B. Reese, The chemical synthesis of oligo- and poly-nucleotides by the phosphotriester approach, Tetrahedron, 34, 21, (3143), (1978).
- P. Cashion, K. Porter, T. Cadger, G. Sathe, T. Tranquilla, H. Notman and E. Jay, Simplification of DNA synthesis by the phosphotriester method, Tetrahedron Letters, 17, 42, (3769), (1976).
- Arthur Myles, Wolfgang Hutzenlaub, Gunther Reitz and Wolfgang Pfleiderer, Nucleotide, I. Synthese und Eigenschaften von Thymidylyl‐(3′ → 3′)‐, ‐(3′ → 5′)‐ und ‐(5′ → 5′)‐thymidin, Chemische Berichte, 108, 9, (2857-2871), (2006).
- J. Engels and W. Pfleiderer, Nucleotide, V: Synthese und eigenschaften von uridin-3′,3′-cyclophosphattriestern, Tetrahedron Letters, 16, 21, (1661), (1975).
- N.J. Cusack, C.B. Reese and J.H. van Boom, Block synthesis of oligonucleotides by the phosphotriester approach, Tetrahedron Letters, 14, 24, (2209), (1973).
- J. Smrt, Protection of the internucleotidic bond after its synthesis. An approach to the synthesis of oligonucleotidic chains., Tetrahedron Letters, 13, 33, (3437), (1972).
- U. Séquin and Ch. Tamm, Nucleosides and Nucleotides. Part 2: Synthesis of both anomers of 1‐(5′‐O‐phosphoryl‐2′‐deoxy‐D‐ribofuranosyl)‐2(1H)‐pyridone [1], Helvetica Chimica Acta, 55, 4, (1196-1218), (2004).
- T. Y. Shen, Nucleoside und Nucleotide als mögliche Therapeutika, Angewandte Chemie, 82, 18, (730-740), (2006).
- T. Y. Shen, Nucleosides and Nucleotides as Potential Therapeutic Agents, Angewandte Chemie International Edition in English, 9, 9, (678-688), (2003).
- Thomas J. Bardos, Chapter 31. Nucleosides and Nucleotides, , 10.1016/S0065-7743(08)60354-1, (333-345), (1970).
- J. Smrt and J. Catlin, Anomaler verlauf der phosphorylierung mit phosphor-säure-methylester-dichlorid, Tetrahedron Letters, 11, 58, (5081), (1970).




