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Organische Chemie

Synthese von Oligodesoxynucleotiden über Phosphorsäuretriester

Fritz Eckstein

Max‐Planck‐Institut für Experimentelle Medizin, Abteilung Chemie, Göttingen

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Ibrahim Rizk

Max‐Planck‐Institut für Experimentelle Medizin, Abteilung Chemie, Göttingen

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First published: Juli 1969
Cited by: 46

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

  • , 6.12 Inorganic Acid Derivatives, Comprehensive Organic Synthesis II, 10.1016/B978-0-08-097742-3.00618-2, (479-554), (2014).
  • , Oligonucleotides and their Derivatives, The Power of Functional Resins in Organic Synthesis, (529-583), (2009).
  • , Gene Synthesis, Total Synthesis of Natural Products, (51-84), (2007).
  • , Oligo- and poly-nucleotides: 50 years of chemical synthesis, Organic & Biomolecular Chemistry, 10.1039/b510458k, 3, 21, (3851), (2005).
  • , 50 Jahre DNA‐Doppelhelix und Miller‐Experiment, Nachrichten aus der Chemie, 51, 6, (666-674), (2010).
  • , The chemical synthesis of oligo- and poly-nucleotides: a personal commentary, Tetrahedron, 10.1016/S0040-4020(02)01084-0, 58, 44, (8893-8920), (2002).
  • , 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).
  • , Bis(2,2,2‐trichloro‐1,1‐dimethylethyl) Phosphorochloridate, Encyclopedia of Reagents for Organic Synthesis, (2001).
  • , The first enzymatic degradation products of the antibiotic moenomycin A., Tetrahedron, 48, 39, (8401), (1992).
  • , Inorganic Acid Derivatives, Comprehensive Organic Synthesis, 10.1016/B978-0-08-052349-1.00167-0, (601-630), (1991).
  • , 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).
  • , [16] An automated DNA synthesizer employing deoxynucleoside 3′-phosphoramidites, Recombinant DNA Part E, 10.1016/0076-6879(87)54082-4, (314-326), (1987).
  • , 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).
  • , The organic chemistry underlying DNA synthesis, Bioorganic Chemistry, 14, 3, (274), (1986).
  • , A total synthesis of yeast alanine transfer RNA, Accounts of Chemical Research, 17, 11, (393), (1984).
  • , Chemical synthesis, cloning and expression of human preproinsulin gene, Journal of Biosciences, 6, 5, (739), (1984).
  • , 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).
  • , DNA synthesis, Tetrahedron, 39, 1, (3), (1983).
  • , , Zeitschrift f�r Chemie, 23, 9, (317-327), (2010).
  • , 3′-3′,3′-5′ and 5′-5′ TpT-Amides: Synthesis, Characterization and Alkaline Hydrolysis, Nucleosides and Nucleotides, 2, 1, (51), (1983).
  • , Darstellung und Konfigurationszuordnung der Diastereomeren des vollständig geschützten 2′‐Desoxyadenylyl‐(3′‐5′)‐2′‐desoxyadenosins, Liebigs Annalen der Chemie, 1982, 7, (1398-1402), (2006).
  • , Phosphoric and phosphinic sulfonic anhydrides – reinvestigation and corrections. Novel methods of synthesis, Chemische Berichte, 115, 4, (1636-1643), (2006).
  • , A simplified strategy for the synthesis of dideoxyribonucleotide blocks, Tetrahedron Letters, 22, 35, (3367), (1981).
  • , , Helvetica Chimica Acta, 64, 5, (1704-1716), (2004).
  • , , Helvetica Chimica Acta, 64, 5, (1688-1703), (2004).
  • , [61] Chemical synthesis of deoxyoligonucleotides by the modified triester method, Nucleic Acids Part I, 10.1016/S0076-6879(80)65063-0, (610-620), (1980).
  • , 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).
  • , , Helvetica Chimica Acta, 62, 4, (1179-1193), (2004).
  • , 8-QUINOLINESULFONYL CHLORIDE: A NEW COUPLING AGENT IN OLIGORIBONUCLEOTIDE SYNTHESIS VIA PHOSPHOTRIESTER APPROACH, Chemistry Letters, 8, 7, (811), (1979).
  • , The Synthesis of Polynucleotides, Advances in Carbohydrate Chemistry and Biochemistry Volume 36, 10.1016/S0065-2318(08)60236-X, (135-213), (1979).
  • , [6] Improved phosphotriester method for the synthesis of gene fragments, Recombinant DNA, 10.1016/0076-6879(79)68008-4, (90-98), (1979).
  • , Synthesis of phospholipids via phosphotriester intermediates, Recueil des Travaux Chimiques des Pays-Bas, 98, 4, (243-250), (2010).
  • , 5-Chloro-8-quinolyl group as high efficient phosphate protecting group for the synthesis of oligoribonucleotides, Tetrahedron Letters, 20, 40, (3857), (1979).
  • , Synthetic Oligodeoxynucleotides for Analyses of DNA Structure and Function, , 10.1016/S0079-6603(08)60268-8, (101-141), (1978).
  • , 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).
  • , The chemical synthesis of oligo- and poly-nucleotides by the phosphotriester approach, Tetrahedron, 34, 21, (3143), (1978).
  • , Simplification of DNA synthesis by the phosphotriester method, Tetrahedron Letters, 17, 42, (3769), (1976).
  • , Nucleotide, I. Synthese und Eigenschaften von Thymidylyl‐(3′ → 3′)‐, ‐(3′ → 5′)‐ und ‐(5′ → 5′)‐thymidin, Chemische Berichte, 108, 9, (2857-2871), (2006).
  • , Nucleotide, V: Synthese und eigenschaften von uridin-3′,3′-cyclophosphattriestern, Tetrahedron Letters, 16, 21, (1661), (1975).
  • , Block synthesis of oligonucleotides by the phosphotriester approach, Tetrahedron Letters, 14, 24, (2209), (1973).
  • , Protection of the internucleotidic bond after its synthesis. An approach to the synthesis of oligonucleotidic chains., Tetrahedron Letters, 13, 33, (3437), (1972).
  • , 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).
  • , Nucleoside und Nucleotide als mögliche Therapeutika, Angewandte Chemie, 82, 18, (730-740), (2006).
  • , Nucleosides and Nucleotides as Potential Therapeutic Agents, Angewandte Chemie International Edition in English, 9, 9, (678-688), (2003).
  • , Chapter 31. Nucleosides and Nucleotides, , 10.1016/S0065-7743(08)60354-1, (333-345), (1970).
  • , Anomaler verlauf der phosphorylierung mit phosphor-säure-methylester-dichlorid, Tetrahedron Letters, 11, 58, (5081), (1970).