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VI. CHEMICAL DEVELOPMENT AND ANALYTICAL CHEMISTRY

A Novel and Economical Synthesis of 2″-O-Alkyl-Uridines

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Pages 1641-1643 | Published online: 16 Aug 2006

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Read on this site (6)

BruceS. Ross, Quanlai Song & Mingming Han. (2005) KILO-SCALE SYNTHESIS PROCESS FOR 2′-O-(2-METHOXYETHYL)-PYRIMIDINE DERIVATIVES. Nucleosides, Nucleotides & Nucleic Acids 24:5-7, pages 815-818.
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Didier Peoc'h, Eric E. Swayze, Balkrishen Bhat & Yogesh S. Sanghvi. (2004) Synthesis of 2′‐Substituted MMI Linked Nucleosidic Dimers: An Optimization Study in Search of High Affinity Oligonucleotides for Use in Antisense Constructs . Nucleosides, Nucleotides & Nucleic Acids 23:1-2, pages 411-438.
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MorrisJ. Robins, Bogdan Doboszewski, BradleyL. Nilsson & MattA. Peterson. (2000) Synthesis of Amide-Linked [(3′)CH2CO-NH(5′)] Nucleoside Analogues of Small Oligonucleotides. Nucleosides, Nucleotides & Nucleic Acids 19:1-2, pages 69-86.
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Atushi Kittaka, Tesuya Kuze, Miori Amano, Hiomichi Tanaka, Taashi Miyasaka, Kuihiko Hirose, Taao Yoshida, Aknori Sarai, Taashi Yasukawa & Shnsuke Ishii. (1999) Introduction of 6-Formylcytidine into a Myb Binding Sequence. Nucleosides and Nucleotides 18:11-12, pages 2769-2783.
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Muthiah Manoharan, AndrewM. Kawasaki, ThazhaP. Prakash, AllisterS. Fraser, Marija Prhavc, GopalB. Inamati, MartinD. Casper & P. Dan Cook. (1999) Carbohydrate Modifications in Antisense Oligonucleotide Therapy: New Kids on the Block. Nucleosides and Nucleotides 18:6-7, pages 1737-1746.
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Atsushi Kittaka, Tetsuya Kuze, Hiromichi Tanaka, Tadashi Miyasaka, Kunihiko Hirose, Tadao Yoshida, Akinori Sarai, Takashi Yasukawa & Shunsuke Ishii. (1999) Oligonucleotides Containing a 6-Substituted Pyrimidine Base: A Design for Myb Inhibitors. Nucleosides and Nucleotides 18:6-7, pages 1501-1502.
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Articles from other publishers (27)

Christopher Liczner, Kieran Duke, Gabrielle Juneau, Martin Egli & Christopher J Wilds. (2021) Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications. Beilstein Journal of Organic Chemistry 17, pages 908-931.
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Zahra Khademi & Kobra Nikoofar. (2020) Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media. RSC Advances 10:51, pages 30314-30397.
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Maurycy Szlenkier & Jerzy Boryski. (2019) Application of Sugar-Base Anhydro Bridge for Modification of Nucleosides in the 2’- and/or 3’-Positions - Revisited. Current Organic Chemistry 23:4, pages 409-438.
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Saswata Karmakar, Tyler Horrocks, Bradley C. Gibbons, Dale C. Guenther, Raymond Emehiser & Patrick J. Hrdlicka. (2019) Synthesis and biophysical characterization of oligonucleotides modified with O2′-alkylated RNA monomers featuring substituted pyrene moieties. Organic & Biomolecular Chemistry 17:3, pages 609-621.
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Tadashi Umemoto, Shinichi Masada, Kenichi Miyata, Mari Ogasawara-Shimizu, Shumpei Murata, Kazunori Nishi, Kazuhiro Ogi, Yoji Hayase & Nobuo Cho. (2017) Direct and practical synthesis of 2′-O,4′-C-aminomethylene-bridged nucleic acid purine derivatives by transglycosylation. Tetrahedron 73:9, pages 1211-1218.
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Patrick J. Hrdlicka & Saswata Karmakar. (2017) 25 years and still going strong: 2′- O -(pyren-1-yl)methylribonucleotides – versatile building blocks for applications in molecular biology, diagnostics and materials science . Organic & Biomolecular Chemistry 15:46, pages 9760-9774.
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Saswata Karmakar, Dale C. Guenther, Bradley C. Gibbons & Patrick J. Hrdlicka. (2017) Recognition of mixed-sequence DNA using double-stranded probes with interstrand zipper arrangements of O2′-triphenylene- and coronene-functionalized RNA monomers. Organic & Biomolecular Chemistry 15:44, pages 9362-9371.
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Saswata Karmakar, Andreas S. Madsen, Dale C. Guenther, Bradley C. Gibbons & Patrick J. Hrdlicka. (2014) Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O 2′-alkylated RNA monomers . Org. Biomol. Chem. 12:39, pages 7758-7773.
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Venubabu Kotikam & Vaijayanti A. Kumar. (2013) Synthesis and properties of 2′-O-[R- and S-(2-amino-3-methoxy)propyl] (R-AMP and S-AMP) nucleic acids. Tetrahedron 69:31, pages 6404-6408.
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Gérald Mathis, Stéphane Bourg, Samia Aci-Sèche, Jean-Christophe Truffert & Ulysse Asseline. (2013) Synthesis and properties of 2′-O-neopentyl modified oligonucleotides. Organic & Biomolecular Chemistry 11:8, pages 1345.
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Saswata Karmakar, Brooke A. Anderson, Rie L. Rathje, Sanne Andersen, Troels B. Jensen, Poul Nielsen & Patrick J. Hrdlicka. (2011) High-Affinity DNA Targeting Using Readily Accessible Mimics of N2′-Functionalized 2′-Amino-α-L-LNA. The Journal of Organic Chemistry 76:17, pages 7119-7131.
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Takeshi Yamada, Natsuki Okaniwa, Hisao Saneyoshi, Akihiro Ohkubo, Kohji Seio, Tetsuya Nagata, Yoshitsugu Aoki, Shin’ichi Takeda & Mitsuo Sekine. (2011) Synthesis of 2′- O -[2-( N -Methylcarbamoyl)ethyl]ribonucleosides Using Oxa-Michael Reaction and Chemical and Biological Properties of Oligonucleotide Derivatives Incorporating These Modified Ribonucleosides . The Journal of Organic Chemistry 76:9, pages 3042-3053.
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Mayumi Takahashi, Noriaki Minakawa & Akira Matsuda. (2009) Synthesis and characterization of 2′-modified-4′-thioRNA: a comprehensive comparison of nuclease stability. Nucleic Acids Research 37:4, pages 1353-1362.
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Thazha P. Prakash, Andrew M. Kawasaki, Edward V. Wancewicz, Lijiang Shen, Brett P. Monia, Bruce S. Ross, Balkrishen Bhat & Muthiah Manoharan. (2008) Comparing In Vitro and In Vivo Activity of 2′- O -[2-(Methylamino)-2-oxoethyl]- and 2′- O -Methoxyethyl-Modified Antisense Oligonucleotides . Journal of Medicinal Chemistry 51:9, pages 2766-2776.
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Qing Dai, John K. Frederiksen, Vernon E. Anderson, Michael E. Harris & Joseph A. Piccirilli. (2007) Efficient Synthesis of [2‘- 18 O]Uridine and Its Incorporation into Oligonucleotides:  A New Tool for Mechanistic Study of Nucleotidyl Transfer Reactions by Isotope Effect Analysis . The Journal of Organic Chemistry 73:1, pages 309-311.
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Hisao Saneyoshi, Itaru Okamoto, Yoshiaki Masaki, Akihiro Ohkubo, Kohji Seio & Mitsuo Sekine. (2007) Facile synthesis of 2′-O-cyanoethyluridine by ring-opening reaction of 2,2′-anhydrouridine with cyanoethyl trimethylsilyl ether in the presence of BF3·Et2O. Tetrahedron Letters 48:48, pages 8554-8557.
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Natsuhisa Oka, Yogesh S. Sanghvi & Emmanuel A. Theodorakis. (2004) 3,3′-Oxybis(dimethoxytrityl chloride) (O-DMTCl): synthesis and applications of a novel bifunctional protecting group. Bioorganic & Medicinal Chemistry Letters 14:12, pages 3241-3244.
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Ken-ichi Takatsuki, Makoto Yamamoto, Sumito Ohgushi, Shigeo Kohmoto, Keiki Kishikawa & Haruhiro Yamashita. (2004) A new protecting group ‘3′,5′-O-sulfinyl’ for xylo-nucleosides. A simple and efficient synthesis of 3′-amino-3′-deoxyadenosine (a puromycin intermediate), 2,2′-anhydro-pyrimidine nucleosides and 2′,3′-anhydro-adenosine. Tetrahedron Letters 45:1, pages 137-140.
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Hiroaki Ozaki, Kiyohiro Nakajima, Kaoru Tatsui, Chieko Izumi, Masayasu Kuwahara & Hiroaki Sawai. (2003) Convenient synthesis of oligodeoxyribonucleotides bearing arabinofuranosyl pyrimidine derivatives and its duplex formation with complementary DNA. Bioorganic & Medicinal Chemistry Letters 13:15, pages 2441-2443.
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Timofei S Zatsepin, Elena A Romanova & Tat'yana S Oretskaya. (2002) Synthesis of 2'- O -alkylnucleosides . Russian Chemical Reviews 71:6, pages 513-534.
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Leonid Beigelman, Peter Haeberli, David Sweedler & Alexander Karpeisky. (2000) Improved Synthetic Approaches Toward 2′-O-Methyl-Adenosine and Guanosine and Their N-Acyl Derivatives. Tetrahedron 56:8, pages 1047-1056.
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Muthiah Manoharan. (1999) 2′-Carbohydrate modifications in antisense oligonucleotide therapy: importance of conformation, configuration and conjugation. Biochimica et Biophysica Acta (BBA) - Gene Structure and Expression 1489:1, pages 117-130.
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Muthiah Manoharan, Thazha P. Prakash, Isabelle Barber-Peoc'h, Balkrishen Bhat, Guillermo Vasquez, Bruce S. Ross & P. Dan Cook. (1999) N -(2-Cyanoethoxycarbonyloxy)succinimide:  A New Reagent for Protection of Amino Groups in Oligonucleotides . The Journal of Organic Chemistry 64:17, pages 6468-6472.
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Urtzi Legorburu, Colin B Reese & Quanlai Song. (1999) Conversion of uridine into 2′-O-(2-methoxyethyl)uridine and 2′-O-(2-methoxyethyl)cytidine. Tetrahedron 55:17, pages 5635-5640.
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Marcel J. J. Blommers, Francois Natt, Wolfgang Jahnke & Bernard Cuenoud. (1998) Dual Recognition of Double-Stranded DNA by 2‘-Aminoethoxy-Modified Oligonucleotides:  The Solution Structure of an Intramolecular Triplex Obtained by NMR Spectroscopy. Biochemistry 37:51, pages 17714-17725.
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Atsushi Kittaka, Tetsuya Kuze, Takashi Asakura, Katsutoshi Ito, Tadashi Miyasaka & Jun-ichiro Inoue. (1998) Oligonucleotides bearing 5-Formyl-2′-O-methyluridine: Preference in binding affinity to the NF-κB (p50) 2 homo- and p50/p65 heterodimers. Bioorganic & Medicinal Chemistry Letters 8:22, pages 3207-3210.
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B. S. ROSS, R. H. SPRINGER, Z. TORTORICI & S. DIMOCK. (2010) ChemInform Abstract: A Novel and Economical Synthesis of 2′‐O‐Alkyl‐uridines. ChemInform 29:10.
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