Recent advances in the syntheses of nucleoside triphosphates

Current Organic Synthesis

Volumn 10, Issue 6, 2013, Pages 903-934

  Kore, Anilkumar R ^a   Srinivasan, Balasubramanian ^a  

^a Life Technologies Corporation   (United States)

Author keywords

Chemical synthesis; Enzymatic synthesis; Nucleoside triphosphates; Phosphorylation; Solid supported synthesis

Indexed keywords

EID: 84894096983     PISSN: 15701794     EISSN: None     Source Type: Journal    
DOI: 10.2174/15701794113109990001     Document Type: Review

References (154)

1. Liu, X.; Takahashi, H.; Harada, Y.; Ogawara, T.; Ogimura, Y.; Mizushina, Y.; Saneyoshi, M.; Yamaguchi, T. 3′-azido-2′,3′- dideoxynucleoside 5′-triphosphates inhibit telomerase activity in vitro, and the corresponding nucleosides cause telomere shortening in human HL60 cells. Nucleic Acid Res., 2007, 35(21), 7140-7149
2. Tomikawa, A.; Seno, M.; Sato-Kiyotaki, K.; Ohtsuki, C.; Hirai, T.; Yamaguchi, T.; Kawaguchi, T.; Yoshida, S.; Saneyoshi, M. Synthetic nucleosides and nucleotides. 40. Selective inhibition of eukaryotic DNA polymerase &alpha by 9-(β-darabinofuranosyl)- 2-(p-n-butylanilino)adenine 5′-triphosphate (BuAaraATP) and its 2′-Up azido analog: Synthesis and enzymatic evaluations. Nucleosides Nucleotides, 1998, 17(1-3), 487-501
3. Furman, R.R.; Hoelzer, D. Purine nucleoside phosphorylase inhibition as a novel therapeutic approach for Bcell lymphoid malignancies. Semin. Oncol., 2007, 34, S29-S34.
4. Lohmann, K. Preparation of adenylpyrophosphoric acid from muscle. Biochem. Z., 1935, 233, 19-36
5. Lohmann, K. The pyrophosphate fraction in the muscle. Naturewiss, 1929, 17, 624-625
6. Fiske, C.H.; Subbarow, Y. Phosphorous compounds of muscle and liver. Science, 1929, 70(1816), 381-382.
7. Gulland, J.M.; Walsh, E.O.F. The structure of adenosine di- and triphosphates. J. Chem. Soc., 1945, 169-172.
8. Baddiley, J.; Michelson, A.M.; Todd, A.R. Nucleotides. Part II. A synthesis of adenosine triphosphate. J. Chem. Soc., 1949, 582-586.
9. Burgess, K.; Cook, D. Syntheses of nucleoside triphosphates. Chem. Rev., 2000, 100(6), 2047-2060.
10. Milewska, Z.; Panusz, H. Quantitative paper chromatography of ribonucleoside mono-, di-, and triphosphates adapted for control of purity of their preparations. Anal. Biochem., 1974, 57(1), 8-13.
11. Johnson, D.C.; Widlanski, T.S. Overview of the synthesis of nucleoside phosphates and polyphosphates. Curr. Protoc. Nucleic Acid Chem., 2004, 13.11.11-13.11.31
12. Morteza, V., Chemical synthesis of nucleoside 5'- triphosphate. In Nucleoside triphosphates and their analogs, CRC Press: 2005; pp 1-22.
13. Haynie, S.; Whitesides, G. Preparation of a mixture of nucleoside triphosphates suitable for use in synthesis of nucleotide phosphate sugars from ribonucleic acid using nuclease P1, a mixture of nucleoside monophosphokinases and acetate kinase. Appl. Biochem. Biotechnol., 1990, 23(3), 205-220
14. Gite, S.U.; Shankar, V. Single-strand-specific nucleases. Crit. Rev. Microbiol., 1995, 21(2), 101-122.
15. Mohamady, S.; Desoky, A.; Taylor, S.D. Sulfonyl imidazolium salts as reagents for the rapid and efficient synthesis of nucleoside polyphosphates and their conjugates. Org. Lett., 2012, 14(1), 402-405.
16. Wu, W.; Freel Meyers, C.L.; Borch, R.F. A novel method for the preparation of nucleoside triphosphates from activated nucleoside phosphoramidates. Org. Lett., 2004, 6(13), 2257-2260.
17. Davisson, V.J.; Woodside, A.B.; Neal, T.R.; Stremler, K.E.; Muehlbacher, M.; Poulter, C.D. Phosphorylation of isoprenoid alcohols. J. Org. Chem., 1986, 51(25), 4768-4779.
18. Shimazu, M.; Shinozuka, K.; Sawai, H. Facile synthesis of nucleotides containing polyphosphates by Mn(II) and Cd(II) ion-catalyzed pyrophosphate bond formation in aqueous solution. Tetrahedron Lett., 1990, 31(2), 235-238.
19. Bogachev, V.S. Synthesis of deoxynucleoside 5'-triphosphates using trifluoroacetic anhydride as an activating reagent. Russ. J. Bioorg.Chem., 1996, 22, 599-604.
20. Mohamady, S.; Jakeman, D.L. An improved method for the synthesis of nucleoside triphosphate analogs. J. Org. Chem., 2005, 70(25), 10588-10591.
21. Risbood, P.A.; Kane Jr, C.T.; Hossain, M.T.; Vadapalli, S.; Chadda, S.K. Synthesis of gemcitabine triphosphate (dFdCTP) as a tris(triethylammonium) salt. Bioorg. Med. Chem. Lett., 2008, 18(9), 2957-2958.
22. Marlow, A.L.; Kiessling, L.L. Improved chemical synthesis of UDPgalactofuranose. Org. Lett., 2001, 3(16), 2517-2519.
23. Zhang, Q.; Liu, H.-W. Studies of UDP-galactopyranose mutase from Escherichia coli: An unusual role of reduced fad in its catalysis. J. Am. Chem. Soc., 2000, 122(38), 9065-9070
24. Tsvetkov, Y.E.; Nikolaev, A.V. The first chemical synthesis of UDP-[α]-D-galactofuranose. J. Chem. Soc., Perkin Trans., 1 2000, (6), 889-891.
25. Mohamady, S.; Taylor, S.D. General procedure for the synthesis of dinucleoside polyphosphates. J. Org. Chem., 2011, 76(15), 6344-6349.
26. Jemielity, J.; Fowler, T.; Zuberek, J.; Stepinski, J.; Lewdorowicz, M.; Niedzwiecka, A.; Stolarski, R.; Darzynkiewicz, E.; Rhoads, R.E. Novel "anti-reverse" cap analogs with superior translational properties. RNA, 2003, 9(9), 1108-1122
27. Stepinski, J.; Waddell, C.; Stolarski, R.; Darzynkiewicz, E.; Rhoads, R.E. Synthesis and properties of mRNAs containing the novel anti-reverse cap analogs 7-methyl(3'-O-methyl)GpppG and 7-methyl (3'- deoxy)GpppG. RNA, 2001, 7(10), 1486-1495.
28. Vasilyeva, 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. Nucleosides, Nucleotides Nucleic Acids, 2011, 30(10), 753-767.
29. Kore, A.R.; Charles, I. Synthesis and evaluation of 2′-O-allyl substituted dinucleotide cap analog for mrna translation. Bioorg. Med. Chem., 2010, 18(22), 8061-8065
30. Kore, A.R.; Shanmugasundaram, M. Synthesis and biological evaluation of trimethyl-substituted cap analogs. Bioorg. Med. Chem. Lett., 2008, 18(3), 880-884
31. Kore, A.R.; Shanmugasundaram, M.; Charles, I.; Cheng, A.M.; Barta, T.J. Synthesis and application of 2′-fluorosubstituted cap analogs. Bioorg. Med. Chem. Lett., 2007, 17(19), 5295-5299
32. 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(17), 4828-4832
33. Kore, A.R.; Shanmugasundaram, M.; Barta, T.J. Synthesis and substrate validation of cap analogs containing 7-deazaguanosine moiety by RNA polymerase. Nucleosides Nucleotides Nucleic Acids, 2010, 29(11-12), 821-830
34. Kore, A.R.; Xiao, Z.; Senthilvelan, A.; Charles, I.; Shanmugasundaram, M.; Mukundarajan, S.; Srinivasan, B. An efficient synthesis of pyrimidine specific 2′-deoxynucleoside-5′-tetraphosphates. Nucleosides Nucleotides Nucleic Acids, 2012, 31(7), 567-573
35. Kore, A.R.; Shanmugasundaram, M.; Charles, I. An efficient synthesis of highly functionalized dinucleotide cap analogs. Tetrahedron Lett., 2012, 53(27), 3518-3520.
36. Jemielity, J.; Pietrowska-Borek, M.; Starzynska, E.; Kowalska, J.; Stolarski, R.; Guranowski, A.; Darzynkiewicz, E. Synthesis and enzymatic characterization of methylene analogs of adenosine 5′-tetraphosphate (p4A). Nucleosides Nucleotides Nucleic Acids, 2005, 24(5-7), 589-593
37. 5-pentaphosphates. Nucleosides Nucleotides Nucleic Acids, 2003, 22(5-8), 691-694
38. Kalek, M.; Jemielity, J.; Grudzien, E.; Zuberek, J.; Bojarska, E.; Cohen, L.S.; Stepinski, J.; Stolarski, R.; Davis, R.E.; Rhoads, R.E.; Darzynkiewicz, E. Synthesis and biochemical properties of novel mRNA 5′ cap analogs resistant to enzymatic hydrolysis. Nucleosides Nucleotides Nucleic Acids, 2005, 24(5-7), 615-621
39. Kowalska, J.; Lewdorowicz, M.; Zuberek, J.; Bojarska, E.; Wojcik, J.; Cohen, L.S.; Davis, R.E.; Stepinski, J.; Stolarski, R.; Darzynkiewicz, E.; Jemielity, J. Synthesis and properties of mRNA cap analogs containing phosphorothioate moiety in 5′,5′-triphosphate chain. Nucleosides Nucleotides Nucleic Acids, 2005, 24(5-7), 595-600
40. Stepinski, J.; Zuberek, J.; Jemielity, J.; Kalek, M.; Stolarski, R.; Darzynkiewicz, E. Novel dinucleoside 5′,5′-triphosphate cap analogs. Synthesis and affinity for murine translation factor eIF4E. Nucleosides Nucleotides Nucleic Acids, 2005, 24(5-7), 629-633.
41. Strenkowska, M.; Wanat, P.; Ziemniak, M.; Jemielity, J.; Kowalska, J. Preparation of synthetically challenging nucleotides using cyanoethyl pimidazolides and microwaves. Org. Lett., 2012, 14(18), 4782-4785.
42. Chamberlain, B.T.; Upton, T.G.; Kashemirov, B.A.; McKenna, C.E. α- Azido bisphosphonates: Synthesis and nucleotide analogs. J. Org. Chem., 2011, 76(12), 5132-5136
43. Ma, Q.F.; Babbitt, P.C.; Kenyon, G.L. Adenosine 5'-[α,β-imido]triphosphate, a substrate for T7 RNA polymerase and rabbit muscle creatine kinase. J. Am. Chem. Soc., 1988, 110(12), 4060-4061.
44. Li, P.; Sergueeva, Z.A.; Dobrikov, M.; Shaw, B.R. Nucleoside and oligonucleoside boranophosphates: Chemistry and properties. Chem. Rev., 2007, 107(11), 4746-4796
45. Ahmadibeni, Y.; Parang, K. Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides. Org. Lett., 2005, 7(25), 5589-5592
46. Zlatev, I.; Lavergne, T.; Debart, F.O.; Vasseur, J.-J.; Manoharan, M.; Morvan, F.O. Efficient solid-phase chemical synthesis of 5′-triphosphates of DNA, RNA, and their analogs. Org. Lett., 2010, 12(10), 2190-2193.
47. Potter, R.L.; Schlesinger, S.; Buettner-Janusch, V.; Thompson, L. The isolation of pyrimidine deoxyribonucleotides from the acid-soluble extract of thymus. J. Biol. Chem., 1957, 226, 381-386
48. Hall, R.H.; Khorana, H.G. Nucleoside polyphosphates. II. A synthesis of uridine-5'-di- and and - triphosphate. J. Am. Chem. Soc., 1954, 76(20), 5056-5060.
49. Smith, M.; Khorana, H.G. Nucleoside polyphosphates. VI. An improved and general method for the synthesis of ribo- and deoxyribonucleoside 5'- triphosphates. J. Am. Chem. Soc., 1958, 80(5), 1141-1145.
50. Ivanov, M. A.; Mukovnya, G.S.L.A.V.; Kochetkov, S.N.; Tunitskaya, V.L.; Alexandrova, L.A. Synthesis and biological properties of pyrimidine 4'- fluoronucleosides and 4'-fluorouridine 5'-O-triphosphate. Russ. J. Bioorg.Chem., 2010, 36(4), 488-496.
51. Ko, H.; Carter, R.L.; Cosyn, L.; Petrelli, R.; de Castro, S.; Besada, P.; Zhou, Y.; Cappellacci, L.; Franchetti, P.; Grifantini, M.; Van Calenbergh, S.; Harden, T.K.; Jacobson, K.A. Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists. Bioorg. Med. Chem., 2008, 16(12), 6319-6332
52. Douglass, J.G.; Patel, R.I.; Yerxa, B.R.; Shaver, S.R.; Watson, P.S.; Bednarski, K.; Plourde, R.; Redick, C.C.; Brubaker, K.; Jones, A.C.; Boyer, J.L. Lipophilic modifications to dinucleoside polyphosphates and nucleotides that confer antagonist properties at the platelet P2Y12 receptor. J. Med. Chem., 2008, 51(4), 1007-1025
53. Ivanov, A.A.; Ko, H.; Cosyn, L.; Maddileti, S.; Besada, P.; Fricks, I.; Costanzi, S.; Harden, T.K.; Van Calenbergh, S.; Jacobson, K.A. Molecular modeling of the human P2Y2 receptor and design of a selective agonist, 2'-amino-2'-deoxy-2-thiouridine 5'-triphosphate. J. Med. Chem., 2007, 50(6), 1166-1176
54. Shaver, S.; Rideout, J.; Pendergast, W.; Douglass, J.; Brown, E.; Boyer, J.; Patel, R.; Redick, C.; Jones, A.; Picher, M.; Yerxa, B. Structure-activity relationships of dinucleotides: Potent and selective agonists of P2Y receptors. Purinergic Signal., 2005, 1(2), 183-191.
55. Moffatt, J.G. A general synthesis of nucleosides-5′ triphosphates. Can. J. Chem., 1964, 42(3), 599-604.
56. Miyashita, T.; Sakata, S.; Hayakawa, H. First synthesis of enantio-uracil dinucleotide, comparison of physicochemical properties of their enantiomers, and separation by chiral column chromatography. Tetrahedron Lett., 2003, 44(47), 8605-8607.
57. Staab, H.A.; Schaller, H.; Cramer, F. Imidazolide der phosphorsäure. Angew. Chem., 1959, 71(23), 736-736
58. Hoard, D.E.; Ott, D.G. Conversion of mono- and oligodeoxyribonucleotides to 5'-triphosphates1. J. Am. Chem. Soc., 1965, 87(8), 1785-1788.
59. Yu. A. Sharkin, D.G.S., L. S. Viktorova, M. K. Kukhanova Synthesis and substrate properties of modified nucleoside 5'-triphosphates mimicking dATP in the reactions of DNA synthesis catalyzed by DNA polymerases. Russ. J. Bioorg. Chem., 2001, 27(5), 340-348.
60. Calleri, E.; Ceruti, S.; Cristalli, G.; Martini, C.; Temporini, C.; Parravicini, C.; Volpini, R.; Daniele, S.; Caccialanza, G.; Lecca, D.; Lambertucci, C.; Trincavelli, M.L.; Marucci, G.; Wainer, I.W.; Ranghino, G.; Fantucci, P.; Abbracchio, M.P.; Massolini, G. Frontal affinity chromatography-mass spectrometry useful for characterization of new ligands for GPR17 receptor. J. Med. Chem., 2010, 53(9), 3489-3501.
61. Imoto, S.; Patro, J.N.; Jiang, Y.L.; Oka, N.; Greenberg, M.M. Synthesis, DNA polymerase incorporation, and enzymatic phosphate hydrolysis of formamidopyrimidine nucleoside triphosphates. J. Am. Chem. Soc., 2006, 128(45), 14606-14611.
62. Iyer, V.V.; Griesgraber, G.W.; Radmer, M.R.; McIntee, E.J.; Wagner, C.R. Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3'-azido-3'-deoxythymidine (AZT). J. Med. Chem., 2000, 43(11), 2266-2274
63. Bollmark, M.; Stawiński, J. A facile access to nucleoside phosphorofluoridate, nucleoside phosphorofluoridothioate, and nucleoside phosphorofluoridodithioate monoesters. Tetrahedron Lett., 1996, 37(32), 5739-5742
64. Kers, I.; Stawiński, J.; Kraszewski, A. A new synthetic method for the preparation of nucleoside phosphoramidate analogs with the nitrogen atom in bridging positions of the phosphoramidate linkage. Tetrahedron Lett., 1998, 39(10), 1219-1222
65. Wada, T.; Mochizuki, A.; Sato, Y.; Sekine, M. A convenient method for phosphorylation involving a facile oxidation of H-phosphonate monoesters via bis(trimethylsilyl) phosphites. Tetrahedron Lett., 1998, 39(39), 7123-7126.
66. Cullis, P.M.; Lee, M. The mechanism of iodine-water oxidation of Hphosphonate diesters. J. Chem. Soc., Chem. Commun., 1992, (17), 1207-1208
67. Nilsson, J.K., A.; Stawinski, J. Chemical and stereochemical aspects of oxidative coupling of H-phosphonate and H-phosphonothioate diesters. Reactions with N,N-, N,O and O,O-binucleophiles. Lett. Org. Chem., 2005, 2(2), 188-197.
68. Sun, Q.; Edathil, J.P.; Wu, R.; Smidansky, E.D.; Cameron, C.E.; Peterson, B.R. One-pot synthesis of nucleoside 5′-triphosphates from nucleoside 5′-Hphosphonates. Org. Lett., 2008, 10(9), 1703-1706.
69. Wu, W.; Bergstrom, D.E.; Davisson, V.J. A combination chemical and enzymatic approach for the preparation of azole carboxamide nucleoside triphosphate. J. Org. Chem., 2003, 68(10), 3860-3865.
70. Guga, P.; Domański, K.; Stec, W.J. Oxathiaphospholane approach to the synthesis of P-chiral, isotopomeric deoxy(ribonucleoside phosphorothioate)s and phosphates labeled with an oxygen isotope. Angew. Chem. Int. Ed., 2001, 40(3), 610-613
71. Baraniak, J.; Kaczmarek, R.; Korczyński, D.; Wasilewska, E. Oxathiaphospholane approach to N- and Ophosphorothioylation of amino acids. J. Org. Chem., 2002, 67(21), 7267- 7274
72. Zmudzka, K.; Nawrot, B.; Chojnacki, T.; Stec, W.J. An oxathiaphospholane approach to one-pot phosphorothioylation of isoprenoid alcohols. Org. Lett., 2004, 6(9), 1385-1387
73. Olesiak, M.K., D.; Wasilewska, E.; Korczyński, D.; Baraniak, J.; Okruszek, A.; Stec, W. J. Thiophosphorylation of biologically relevant alcohols by the oxathiaphospholane approach. Synlett, 2002, 967-971.
74. Misiura, K.; Szymanowicz, D.; Stec, W.J. Synthesis of nucleoside α- thiotriphosphates via an oxathiaphospholane approach. Org. Lett., 2005, 7(11), 2217-2220.
75. Woźniak, L.A.; Koziołkiewicz, M.; Kobylańska, A.; Stec, W.J. Potassium peroxymonosulfate (oxone) - an efficient oxidizing agent for phosphothio compounds. Bioorg. Med. Chem. Lett., 1998, 8(19), 2641-2646.
76. Ludwig, J.; Eckstein, F. Rapid and efficient synthesis of nucleoside 5'-O-(1- thiotriphosphates), 5'-triphosphates and 2',3'-cyclophosphorothioates using 2- chloro-4H-1,3,2-benzodioxaphosphorin-4-one. J. Org. Chem., 1989, 54(3), 631-635.
77. Jurczyk, S.C.; Kodra, J.T.; Park, J.-H.; Benner, S.A.; Battersby, T.R. Synthesis of 2′-deoxyisoguanosine 5′-triphosphate and 2′-deoxy-5- methylisocytidine 5′-triphosphate. Helv. Chim. Acta., 1999, 82(7), 1005-1015.
78. Trévisiol, E.; Defrancq, E.; Lhomme, J.; Laayoun, A.; Cros, P. Synthesis of methylketone containing nucleoside triphosphates for RNA labelling. Tetrahedron 2000, 56(35), 6501-6510.
79. Schoetzau, T.; Langner, J.; Moyroud, E.; Roehl, I.; Vonhoff, S.; Klussmann, S. Aminomodified nucleobases: Functionalized nucleoside triphosphates applicable for SELEX. Bioconjugate Chem., 2003, 14(5), 919-926.
80. Hutter, D.; Kim, M.-J.; Karalkar, N.; Leal, N.A.; Chen, F.; Guggenheim, E.; Visalakshi, V.; Olejnik, J.; Gordon, S.; Benner, S.A. Labeled nucleoside triphosphates with reversibly terminating aminoalkoxyl groups. Nucleosides Nucleotides Nucleic Acids, 2010, 29(11-12), 879-895.
81. Hollenstein, M. Synthesis of deoxynucleoside triphosphates that include proline, urea, or sulfonamide groups and their polymerase incorporation into DNA. Chem. Eur. J., 2012, 18(42), 13320-13330.
82. Zou, K.; Horhota, A.; Yu, B.; Szostak, J.W.; McLaughlin, L.W. Synthesis of α-L-threofuranosyl nucleoside triphosphates (tNTPs). Org. Lett., 2005, 7(8), 1485-1487.
83. Schöning, K.-U.; Scholz, P.; Guntha, S.; Wu, X.; Krishnamurthy, R.; Eschenmoser, A. Chemical etiology of nucleic acid structure: The α- threofuranosyl-(3'→2') oligonucleotide system. Science 2000, 290(5495), 1347-1351.
84. Schöning, K.-U.; Scholz, P.; Wu, X.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. The α-L-threofuranosyl-(3'→2)- oligonucleotide system ('TNA'): Synthesis and pairing properties. Helv. Chim. Acta., 2002, 85(12), 4111-4153.
85. Lin, J.; Porter, K.W.; Shaw, B.R. Synthesis and properties of novel triphosphate analogs: Ribonucleoside and deoxyribonucleoside (α-P-borano, α-P-thio)triphosphates. Nucleosides Nucleotides Nucleic Acids, 2001, 20(4- 7), 1019-1023.
86. Wang, G.; Boyle, N.; Chen, F.; Rajappan, V.; Fagan, P.; Brooks, J.L.; Hurd, T.; Leeds, J.M.; Rajwanshi, V.K.; Jin, Y.; Prhavc, M.; Bruice, T.W.; Cook, P.D. Synthesis of AZT 5'-triphosphate mimics and their inhibitory effects on HIV-1 reverse transcriptase. J. Med. Chem., 2004, 47(27), 6902-6913.
87. Meena; Sam, M.; Pierce, K.; Szostak, J.W.; McLaughlin, L.W. 2′,3′-dideoxy- 3′-thionucleoside triphosphates: Syntheses and polymerase substrate activities. Org. Lett., 2007, 9(6), 1161-1163.
88. Jiang, C.; Li, B.; Guan, Z.; Yang, Z.; Zhang, L.; Zhang, L. Synthesis and recognition of novel isonucleoside triphosphates by DNA polymerases. Bioorg. Med. Chem., 2007, 15(8), 3019-3025
89. Xu, K.; Min, J.; Zhang, L. Synthesis of isonucleoside 5′-triphosphates. Synth. Commun., 2003, 33(11), 1905-1910.
90. Horhota, A.T.; Szostak, J.W.; McLaughlin, L.W. Glycerol nucleoside triphosphates: Synthesis and polymerase substrate activities. Org. Lett., 2006, 8(23), 5345-5347.
91. Vaish, N.K.; Fraley, A.W.; Szostak, J.W.; McLaughlin, L.W. Expanding the structural and functional diversity of RNA: Analog uridine triphosphates as candidates for in vitro selection of nucleic acids. Nucleic Acid Res., 2000, 28(17), 3316-3322.
92. Han, Q.; Gaffney, B.L.; Jones, R.A. One-flask synthesis of dinucleoside tetra- and pentaphosphates. Org. Lett., 2006, 8(10), 2075-2077.
93. Roucairol, C.; Azoulay, S.; Nevers, M.-C.; Golebiowski, J.; Créminon, C.; Grassi, J.; Burger, A.; Duval, D. Design, synthesis and studies of triphosphate analogs for the production of anti AZT-TP antibodies. Bioorg. Med. Chem. Lett., 2010, 20(3), 987-990
94. He, K.; Hasan, A.; Krzyzanowska, B.; Shaw, B.R. Synthesis and separation of diastereomers of ribonucleoside 5'-(α-P-borano)triphosphates. J. Org. Chem., 1998, 63(17), 5769-5773.
95. Caton-Williams, J.; Lin, L.; Smith, M.; Huang, Z. Convenient synthesis of nucleoside 5′-triphosphates for RNA transcription. Chem. Commun., 2011, 47(28), 8142-8144
96. Caton-Williams, J.; Smith, M.; Carrasco, N.; Huang, Z. Protection-free one-pot synthesis of 2′-deoxynucleoside 5′-triphosphates and DNA polymerization. Org. Lett., 2011, 13(16), 4156-4159.
97. Boyle, N.A.; Rajwanshi, V.K.; Prhavc, M.; Wang, G.; Fagan, P.; Chen, F.; Ewing, G.J.; Brooks, J.L.; Hurd, T.; Leeds, J.M.; Bruice, T.W.; Cook, P.D. Synthesis of 2',3'-dideoxynucleoside 5′-α-P-borano-β,γ- (difluoromethylene)triphosphates and their inhibition of HIV-1 reverse transcriptase. J. Med. Chem., 2005, 48(7), 2695-2700
98. Nahum, V.; Zündorf, G.; Lévesque, S.A.; Beaudoin, A.R.; Reiser, G.; Fischer, B. Adenosine 5′-O-(1-boranotriphosphate) derivatives as novel P2Y1 receptor agonists. J. Med. Chem., 2002, 45(24), 5384-5396.
99. Wolf, S.; Zismann, T.; Lunau, N.; Warnecke, S.; Wendicke, S.; Meier, C. A convenient synthesis of nucleoside diphosphate glycopyranoses and other polyphosphorylated bioconjugates. Eur. J. Cell Biol., 2010, 89(1), 63-75
100. Warnecke, S.; Meier, C. Synthesis of nucleoside di- and triphosphates and dinucleoside polyphosphates with cycloSal-nucleotides. J. Org. Chem., 2009, 74(8), 3024-3030
101. Warnecke, S.; Meier, C. New and efficient synthesis of nucleoside polyphosphates and nucleoside monophosphate sugars. Nucleic Acids Symp. Ser., 2008, 52(1), 583-584.
102. Meier, C. CycloSal phosphates as chemical trojan horses for intracellular nucleotide and glycosylmonophosphate delivery-chemistry meets biology. Eur. J. Org. Chem., 2006, 2006(5), 1081-1102.
103. Wendicke, S.; Warnecke, S.; Meier, C. Efficient synthesis of nucleoside diphosphate glycopyranoses. Angew. Chem. Int. Ed., 2008, 47(8), 1500-1502.
104. Arlt, M.; Hindsgaul, O. Rapid chemical synthesis of sugar nucleotides in a form suitable for enzymic oligosaccharide synthesis. J. Org. Chem., 1995, 60(1), 14-15
105. Schäfer, A.; Thiem, J. Synthesis of novel donor mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as potential transferase inhibitors. J. Org. Chem., 1999, 65(1), 24-29
106. Moffatt, J.G.; Khorana, H.G. Nucleoside polyphosphates. VIII. New and improved syntheses of uridine diphosphate glucose and flavin adenine dinucleotide using nucleoside-5' phosphoramidates. J. Am. Chem. Soc., 1958, 80(14), 3756-3761
107. Roseman, S.; Distler, J.J.; Moffatt, J.G.; Khorana, H.G. Nucleoside polyphosphates. XI. An improved general method for the synthesis of nucleotide coenzymes. Syntheses of uridine-5', cytidine-5' and guanosine-5' diphosphate derivatives. J. Am. Chem. Soc., 1961, 83(3), 659-663.
108. Yoshikawa, M.; Kato, T.; Takenishi, T. A novel method for phosphorylation of nucleosides to 5'-nucleotides. Tetrahedron Lett., 1967, 8(50), 5065-5068.
109. Cramer, F.; Winter, M. Imidoester, VI. Katalytische wirkung von dimethylformamid bei reaktionen von phosphorsäureester-chloriden. Chem. Ber., 1961, 94(4), 989-996.
110. Ludwig, J. A new route to nucleoside 5'-triphosphates. Acta. Biochim. Biophy. Acad. Hung. 1981, 16, 131-133.
111. Abramova, T.V.; Vasileva, S.V.; Koroleva, L.S.; Kasatkina, N.S.; Silnikov, V.N. Design and synthesis of dinucleotide 5′-triphosphates with expanded functionality. Bioorg. Med. Chem., 2008, 16(20), 9127-9132.
112. 6 receptors. J. Med. Chem., 2006, 49(24), 7076-7087.
113. Shi, J.; Zhou, L.; Zhang, H.; McBrayer, T.R.; Detorio, M.A.; Johns, M.; Bassit, L.; Powdrill, M.H.; Whitaker, T.; Coats, S.J.; Götte, M.; Schinazi, R.F. Synthesis and antiviral activity of 2′-deoxy-2′-fluoro-2′-C-methyl-7- deazapurine nucleosides, their phosphoramidate prodrugs and 5′- triphosphates. Bioorg. Med. Chem. Lett., 2011, 21(23), 7094-7098.
114. Roychowdhury, A.; Illangkoon, H.; Hendrickson, C.L.; Benner, S.A. 2′- deoxycytidines carrying amino and thiol functionality: Synthesis and incorporation by vent (exo-) polymerase. Org. Lett., 2004, 6(4), 489-492.
115. Riedl, J.; Horáková, P.; Šebest, P.; Pohl, R.; Havran, L.; Fojta, M.; Hocek, M. Tetrathiafulvalene-labelled nucleosides and nucleoside triphosphates: Synthesis, electrochemistry and the scope of their polymerase incorporation into DNA. Eur. J. Org. Chem., 2009, 2009(21), 3519-3525.
116. Santner, T.; Siegmund, V.; Marx, A.; Micura, R. The synthesis of 2'- methylseleno adenosine and guanosine 5'-triphosphates. Bioorg. Med. Chem., 2012, 20(7), 2416-2418.
117. Moriyama, K.; Suzuki, T.; Negishi, K.; Graci, J.D.; Thompson, C.N.; Cameron, C.E.; Watanabe, M. Effects of introduction of hydrophobic group on ribavirin base on mutation induction and anti-RNA viral activity. J. Med. Chem., 2008, 51(1), 159-166.
118. Okamoto, A.; Tanaka, K.; Nishiza, K.-I.; Saito, I. Synthesis of an artificial hole-transporting nucleoside triphosphate, dmdatp, and its enzymatic incorporation into DNA. Bioorg. Med. Chem., 2004, 12(22), 5875-5880.
119. Nairne, R.J.D.; Pickering, L.; Smith, C.L. Synthesis of pyrrole carboxamide nucleotide triphosphates: Putative labelled nucleotide analogs. Tetrahedron Lett., 2002, 43(12), 2289-2291.
120. Mishra, N.C.; Broom, A.D. A novel synthesis of nucleoside 5′-triphosphates. J. Chem. Soc., Chem. Commun., 1991, (18), 1276-1277.
121. Hoffmann, C.; Genieser, H.G.; Veron, M.; Jastorff, B. Novel synthesis of nucleoside 5'-polyphosphates. Bioorg. Med. Chem. Lett., 1996, 6(21), 2571-2574.
122. Jansen, R.S.; Rosing, H.; Schellens, J.H.M.; Beijnen, J.H. Facile small scale synthesis of nucleoside 5'-phosphate mixtures. Nucleosides Nucleotides Nucleic Acids, 2010, 29(1), 14-26.
123. Collier, A.; Wagner, G. A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). Org. Biomol. Chem., 2006, 4(24), 4526-4532.
124. Gillerman, I.; Fischer, B. An improved one-pot synthesis of nucleoside 5′- triphosphate analogs. Nucleosides Nucleotides Nucleic Acids, 2010, 29(3), 245-256.
125. Kore, A.R.; Shanmugasundaram, M.; Senthilvelan, A.; Srinivasan, B. An improved protection-free one-pot chemical synthesis of 2′-deoxynucleoside- ′-triphosphates. Nucleosides Nucleotides Nucleic Acids, 2012, 31(5), 423-431.
126. Kore, A.R.; Shanmugasundaram, M.; Senthilvelan, A.; Srinivasan, B. Gramscale chemical synthesis of 2′-deoxynucleoside-5′-O-triphosphates. Curr. Protoc. Nucleic Acid Chem., 2012, 13.10.11-13.10.12.
127. Kore, A.R.; Shanmugasundaram, M. Highly stereoselective palladiumcatalyzed heck coupling of 5-iodouridine-5′-triphosphates with allylamine: A new efficient method for the synthesis of (E)-5-aminoallyl-uridine-5′- triphosphates. Tetrahedron Lett., 2012, 53(20), 2530-2532.
128. 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(24), 3070-3072.
129. Kore, A.R.; Senthilvelan, A.; Shanmugasundaram, M. A new, facile, and protection-free one-pot chemical synthesis of 2′-deoxynucleoside-5′- tetraphosphates. Tetrahedron Lett., 2012, 53(44), 5868-5870.
130. Kore, A.R.; Srinivasan, B. Efficient synthesis of 3-cyanovinylcarbazole-1′-β- deoxyriboside-5′-triphosphate: A reversible photo-cross-linking probe. Tetrahedron Lett., 2012, 53(31), 4012-4014.
131. Venkatesan, N.; Kim, B.H. Peptide conjugates of oligonucleotides: Synthesis and applications. Chem. Rev., 2006, 106(9), 3712-3761.
132. Ahmadibeni, Y.; Parang, K. Synthesis and evaluation of modified oligodeoxynucleotides containing diphosphodiester internucleotide linkages. Angew. Chem. Int. Ed., 2007, 46(25), 4739-4743
133. Dash, C.; Ahmadibeni, Y.; Hanley, M.J.; Pandhare, J.; Gotte, M.; Le Grice, S.F.J.; Parang, K. Inhibition of multi-drug resistant HIV-1 reverse transcriptase by nucleoside β-triphosphates. Bioorg. Med. Chem. Lett., 2011, 21(12), 3519-3522
134. Ahmadibeni, Y.; Parang, K. Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides. J. Org. Chem., 2005, 70(3), 1100-1103
135. Ahmadibeni, Y.; Parang, K. Application of a solid-phase β-triphosphitylating reagent in the synthesis of nucleoside β- triphosphates. J. Org. Chem., 2006, 71(15), 5837-5839
136. Ahmadibeni, Y.; Parang, K. Solid-phase synthesis of dinucleoside and nucleosidecarbohydrate phosphodiesters and thiophosphodiesters. J. Org. Chem., 2006, 71(17), 6693-6696
137. Ahmadibeni, Y.; Parang, K. Polymer-bound oxathiaphospholane: A solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates. Org. Lett., 2005, 7(10), 1955-1958
138. Ahmadibeni, Y.; Parang, K. Solid-phase synthesis of symmetrical 5′,5′- dinucleoside mono-, di-, tri-, and tetraphosphodiesters. Org. Lett., 2007, 9(22), 4483-4486
139. Ahmadibeni, Y.; Dash, C.; Le Grice, S.F.J.; Parang, K. Solid-phase synthesis of 5′-O-β,γ-methylenetriphosphate derivatives of nucleosides and evaluation of their inhibitory activity against HIV-1 reverse transcriptase. Tetrahedron Lett., 2010, 51(22), 3010-3013.
140. Lebedev, A.V.; Koukhareva, I.I.; Beck, T.; Vaghefi, M.M. Preparation of oligodeoxynucleotide 5′-triphosphates using solid support approach. Nucleosides Nucleotides Nucleic Acids, 2001, 20(4-7), 1403-1409.
141. Toy, P.H.; Janda, K.D. Soluble polymer-supported organic synthesis. Acc. Chem. Res., 2000, 33(8), 546-554
142. Gravert, D.J.; Janda, K.D. Organic synthesis on soluble polymer supports: Liquid-phase methodologies. Chem. Rev., 1997, 97(2), 489-510.
143. Crauste, C.L.; Périgaud, C.; Peyrottes, S. Insights into the soluble PEGsupported synthesis of cytosine-containing nucleoside 5′-mono-, di-, and triphosphates. J. Org. Chem., 2009, 74(23), 9165-9172.
144. Lieberman, I.; Kornberg, A.; Simms, E.S. Enzymatic synthesis of nucleoside diphosphates and triphosphates. J. Biol. Chem., 1955, 215, 429-440.
145. Staffan, E., Enzymatic synthesis of nucleoside triphosphates. In Nucleoside triphosphates and their analogs, CRC Press: 2005; pp 23-37.
146. Howhan, P.; Pornbanlualap, S. Cloning and effective induction of escherichia coli nucleoside diphosphate kinase by lactose. Science Asia 2003, 29, 347-353.
147. Kamiya, H.; Kasai, H. Preparation of 8-hydroxy-dGTP and 2-hydroxy-dATP by a phosphate transfer reaction by nucleoside-diphosphate kinase. Nucleosides Nucleotides, 1999, 18(3), 307-310.
148. Wu, Y.; Fa, M.; Tae, E.L.; Schultz, P.G.; Romesberg, F.E. Enzymatic phosphorylation of unnatural nucleosides. J. Am. Chem. Soc., 2002, 124(49), 14626-14630.
149. Van Rompay, A.R.; Johansson, M.; Karlsson, A. Phosphorylation of nucleosides and nucleoside analogs by mammalian nucleoside monophosphate kinases. Pharmacol. Therap., 2000, 87(2-3), 189-198.
150. Schneider, B.; Babolat, M.; Xu, Y.W.; Janin, J.; Véron, M.; Deville-Bonne, D. Mechanism of phosphoryl transfer by nucleoside diphosphate kinase. Eur. J. Biochem., 2001, 268(7), 1964-1971.
151. Wu, W.; Bergstrom, D.E.; Jo Davisson, V. Chemoenzymatic preparation of nucleoside triphosphates. Curr. Protoc. Nucleic Acid Chem. 2004, 13.12.11- 13.12.19.
152. Davisson, V.J.; Davis, D.R.; Dixit, V.M.; Poulter, C.D. Synthesis of nucleotide 5'-diphosphates from 5'-O-tosyl nucleosides. J. Org. Chem., 1987, 52(9), 1794-1801.
153. Schultheisz, H.L.; Szymczyna, B.R.; Scott, L.G.; Williamson, J.R. Pathway engineered enzymatic de novo purine nucleotide synthesis. ACS Chem. Biol., 2008, 3(8), 499-511.
154. Schultheisz, H.L.; Szymczyna, B.R.; Scott, L.G.; Williamson, J.R. Enzymatic de novo pyrimidine nucleotide synthesis. J. Am. Chem. Soc., 2010, 133(2), 297-304.