Highly Regioselective C-5 Iodination of Pyrimidine Nucleotides and Subsequent Chemoselective Sonogashira Coupling with Propargylamine

REFERENCES

• Blackburn, G.M.; Gait, M.J.; Loakes, D; Williams, D.M. Nucleic Acids in Chemistry and Biology, Royal Society of Chemistry: London, 2006.
   Google Scholar
• Kore, A.R.; Charles, I. Recent developments in the synthesis and applications of C5-substituted pyrimidine nucleosides and nucleotides. Current Org. Chem. 2012, 16, 1996–2013.
   Web of Science ®Google Scholar
• Vaghefi, M. Nucleoside Triphosphates and their Analogs, CRC Press, Taylor and Francis Group, Boca Raton, 2005.
   Google Scholar
• Cox, W.G.; Singer, V.L. Fluorescent DNA hybridization probe preparation using amine modification and reactive dye coupling. BioTechniques 2004, 36, 114–122.
   PubMed Web of Science ®Google Scholar
• Heng, H.H.; Spyropoulos, B.; Moens, P.B. FISH technology in chromosome and genome research. Bioessays 1997, 19, 75–84.
   PubMed Web of Science ®Google Scholar
• Brown, P.O.; Botstein, D. Gene expression informatics – it's all in your mine. Nat. Genet. 1999, 21, 33–37.
   PubMed Web of Science ®Google Scholar
• Lockhart, D.J.; Winzeler, E.A. Genomics, gene expression and DNA assays. Nature 2000, 405, 827–836.
   PubMed Web of Science ®Google Scholar
• Hanna, M.M.; Yuriev, E.; Zhang, J.; Riggs, D.L. Probing the environment of nascent RNA in Escherichia coli transcription elongation complexes utilizing a new fluorescent ribonucleotide analog. Nuc. Acids Res. 1999, 27, 1369–1376.
   PubMed Web of Science ®Google Scholar
• Brazier, J.A.; Shibata, T.; Townsley, J.; Taylor, B.F.; Frary, E.; Williams, N.H.; Williams, D.M.NA Amino-functionalized DNA: the properties of C5-amino-alkyl substituted 2’-deoxyuridines and their application in DNA triplex formation. Nuc. Acids Res. 2005, 33, 1362–1371.
   PubMed Web of Science ®Google Scholar
• Cahová, H.; Havran, L.; Brázdilová, P.; Pivoňková, H.; Pohl, R.; Fojta, M.; Hocek, M. Aminophenyl- and nitrophenyl-labeled nucleoside triphosphates: Synthesis, enzymatic incorporation, and electrochemical detection. Angew. Chem. Int. Ed. 2008, 47, 2059–2062.
   PubMed Web of Science ®Google Scholar
• Kumar, R.; Wiebe, L.I.; Knaus, E.E. A mild and efficient methodology for the synthesis of 5-halogeno uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate. Can. J. Chem. 1994, 72, 2005–2010.
   Web of Science ®Google Scholar
• Agrofoglio, L.A.; Gillaizeau, I.; Saito, Y. Palladium-assisted routes to nucleotides. Chem. Rev. 2003, 103, 1875–1916.
   PubMed Web of Science ®Google Scholar
• Chinchilla, R.; Nájera, C. Recent advances in Sonogashira reactions. Chem. Soc. Rev. 2011, 40, 5084–5121.
   PubMed Web of Science ®Google Scholar
• Jager, S.; Rasched, G.; Kornreich-Leshem, H.; Engeser, M.; Thum, O.; Famulok, M. A versatile toolbox for variable DNA functionalization at high density. J. Am. Chem. Soc. 2005, 127, 15071–15082.
   PubMed Web of Science ®Google Scholar
• Borsenberger, V.; Kukwikila, M.; Howorka, S. Synthesis and enzymatic incorporation of modified deoxyuridine triphosphates. Org. Biomol. Chem. 2009, 7, 3826–3835.
   PubMed Web of Science ®Google Scholar
• Matulic-Adamic, J.; Daniher, A.T.; Karpeisky, A.; Haeberli, P.; Sweedler, D.; Beigelman, L. Functionalized nucleoside 5′-triphosphates for in vitro selection of new catalytic ribonucleic acids. Bioorganic Med. Chem. Lett. 2000, 10, 1299–1302.
   PubMed Web of Science ®Google Scholar
• Garg, N.K.; Woodroofe, C.C.; Lacenere, J.; Quake, S.R.; Stoltz, B.M. A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry. Chem. Commun. 2005, 4551–4553.
   PubMed Web of Science ®Google Scholar
• Vailyeva, S.V.; Budilkin, B.I.; Konevetz, D.A.; Silnikov, V.N. Synthesis of novel nucleoside 5′-triphosphates and phosphoramidites containing alkyne or amino groups for the postsynthetic functionalization of nucleic acids. Nucleos. Nucleot Nucl. Acids 2011, 30, 753–767.
   PubMed Web of Science ®Google Scholar
• Kielkowski, P.; Pohl, R.; Hocek, M. Synthesis of acetylene linked double-nucleobase nucleos(t)ide building blocks and polymerase construction of DNA containing cytosines in the major groove. J. Org. Chem. 2011, 76, 3457–3462.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Shanmugasundaram, M.; Vlassov, A.V. Synthesis and application of a new 2′, 3′-isopropylidene guanosine substituted cap analog. Bioorg. Med. Chem. Lett. 2008, 18, 4828–4832.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Charles, I.; Shanmugasundaram, M. Synthesis and application of 2′-ara-fluoroguanosine-substituted cap analog. Chem. Lett. 2009, 38, 652–653.
   Web of Science ®Google Scholar
• Kore, A.R.; Shanmugasundaram, M.; Charles, I.; Vlassov, A.V.; Barta, T.J. Locked nucleic acid (LNA)-modified dinucleotide mRNA cap analogue: synthesis, enzymatic incorporation, and utilization. J. Am. Chem. Soc. 2009, 131, 6364–6365.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Shanmugasundaram, M.; Senthilvelan, A.; Srinivasan, B. An improved protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′-triphosphates. Nucleos. Nucleot. Nucl. Acids 2012, 31, 423–431.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Xiao, Z.; Senthilvelan, A.; Charles, I.; Shanmugasundaram, M.; Mukundarajan, S.; Srinivasan, B. An efficient synthesis of pyrimidine specific 2′-deoxynucleoside-5y-tetraphosphates. Nucleos. Nucleot. Nucl. Acids 2012, 31, 567–573.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Senthilvelan, A.; Srinivasan, B.; Shanmugasundaram, M. Facile protection-free one-pot chemical synthesis of nucleoside-5′-tetraphosphates. Nucleos. Nucleot. Nucl. Acids 2013, 32, 411–420.
   PubMed Web of Science ®Google Scholar
• Kore, A.R.; Shanmugasundaram, M. Highly stereoselective palladium-catalyzed Heck coupling of 5-iodo-uridine triphosphates with allylamine: a new efficient method for the synthesis of (E)-5-aminoallyl-uridine triphosphates. Tetrahedron Lett. 2012, 53, 2530–2532.
   Web of Science ®Google Scholar
• Kore, A.R.; Senthilvelan, A.; Shanmugasundaram, M. Highly chemoselective palladium-catalyzed Sonogashira coupling of 5-iodouridine-5′-triphosphates with propargylamine: a new efficient method for the synthesis of 5-aminopropargyl-uridine-5′-triphosphates. Tetrahedron Lett. 2012, 53, 3070–3072.
   Web of Science ®Google Scholar
• Bahlaouan, Z.; Thibonnet, J.; Duchêne, A.; Parrain, J.-L.; Elhilali, M.; Abarbri, M. Efficient preparation of ortho-aminobenzenesulfonamides using ligand-free copper(I)-catalyzed amination. Syn. Lett. 2011, 17, 2509–2512.
   Google Scholar