Synthesis and properties of 2′-deoxy-2′,4′-difluoroarabinose-modified nucleic acids

Journal of Organic Chemistry

Volumn 80, Issue 6, 2015, Pages 3083-3091

  Martínez Montero, Saúl ^a   Deleavey, Glen F ^a   Dierker Viik, Arden ^a   Lindovska, Petra ^a   Ilina, Tatiana ^b   Portella, Guillem ^c   Orozco, Modesto ^c   Parniak, Michael A ^b   González, Carlos ^d   Damha, Masad J ^a  

^a MCGILL UNIVERSITY   (Canada)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF BARCELONA   (Spain)

^d INSTITUTO DE QUÍMICA FÍSICA ROCASOLANO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DISEASES; DNA; FLUORINE; NUCLEOTIDES; QUANTUM THEORY; RNA;

DNA STRANDS; DNA-RNA HYBRIDS; HIV REVERSE TRANSCRIPTASE; NMR ANALYSIS; QUANTUM-MECHANICAL CALCULATION; RNASE H; STEREO-SELECTIVE; SUGAR PUCKER;

NUCLEIC ACIDS;

2' DEOXY 2',4' DIFLUOROARABINOSE; ARABINOSE DERIVATIVE; MONOMER; NUCLEOSIDE; RIBONUCLEASE H; RNA DERIVATIVE; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; 2'-DEOXY-2',4'-DIFLUOROARABINOSE; ARABINOSE; DNA; RNA;

ARTICLE; DNA STRAND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RNA HYBRIDIZATION; STEREOCHEMISTRY; SYNTHESIS; THERMOSTABILITY; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY;

ARABINOSE; DNA; MOLECULAR STRUCTURE; RNA;

EID: 84925372627     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502948t     Document Type: Article

References (39)

1. Deleavey, G. F.; Damha, M. J. Chem. Biol. 2012, 19, 937-954
2. Watts, J. K.; Corey, D. R. J. Pathol. 2012, 226, 365-379
3. McGowan, M. P.; Tardif, J. C.; Ceska, R.; Burgess, L. J.; Soran, H.; Gouni-Berthold, I.; Wagener, G.; Chasan-Taber, S. Plos One 2012, 7, e49006
4. Bramse, J. B.; Grünweller, A.; Hartmann, R. K.; Kjems, J. Using chemical modification to enhance siRNA performance. In Handbook of RNA Biochemistry, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2014; pp 1243-1278.
5. Burnett, J. C.; Rossi, J. J. Chem. Biol. 2012, 19, 60-71
6. Sharma, V. K.; Sharma, R. K.; Singh, S. K. Med. Chem. Commum. 2014, 5, 1454-1471
7. Kawasaki, A. M.; Casper, M. D.; Freier, S. M.; Lesnik, E. A.; Zounes, M. C.; Cummins, L. L.; Gonzalez, C.; Cook, P. D. J. Med. Chem. 1993, 36, 831-841
8. Williams, D. M.; Benseler, F.; Eckstein, F. Biochemistry 1991, 30, 4001-4009
9. Watts, J. K.; Sadalapure, K.; Choubdar, N.; Pinto, B. M.; Damha, M. J. J. Org. Chem. 2006, 71, 921-925
10. Anzahaee, M. Y.; Watts, J. K.; Alla, N. R.; Nicholson, A. W.; Damha, M. J. J. Am. Chem. Soc. 2011, 133, 728-731
11. Damha, M. J.; Wilds, C. J.; Noronha, A.; Brukner, I.; Borkow, G.; Arion, D.; Parniak, M. A. J. Am. Chem. Soc. 1998, 120, 13545-13545
12. Mangos, M. M.; Min, K. L.; Viazovkina, E.; Galarneau, A.; Elzagheid, M. I.; Parniak, M. A.; Damha, M. J. J. Am. Chem. Soc. 2003, 125, 654-661
13. Kois, P.; Tocik, Z.; Spassova, M.; Ren, W. Y.; Rosenberg, I.; Soler, J. F.; Watanabe, K. A. Nucleosides Nucleotides 1993, 12, 1093-1109
14. Watts, J. K.; Martin-Pintado, N.; Gomez-Pinto, I.; Schwartzentruber, J.; Portella, G.; Orozco, M.; Gonzalez, C.; Damha, M. J. Nucleic Acids Res. 2010, 38, 2498-2511
15. Dudley, A.; Sater, M.; Le, P. U.; Trinh, G.; Sadr, M. S.; Bergeron, J.; Deleavey, G. F.; Bedell, B.; Damha, M. J.; Petrecca, K. Oncogene 2014, 33, 4952-4960
16. Fortin, M.; DAnjou, H.; Higgins, M. E.; Gougeon, J.; Aube, P.; Moktefi, K.; Mouissi, S.; Seguin, S.; Seguin, R.; Renzi, P. M.; Paquet, L.; Ferrari, N. Resp. Res. 2009, 10, 39
17. Martinez-Montero, S.; Deleavey, G. F.; Kulkarni, A.; Martin-Pintado, N.; Lindovska, P.; Thomson, M.; Gonzalez, C.; Gotte, M.; Damha, M. J. J. Org. Chem. 2014, 79, 5627-5635
18. Thibaudeau, C.; Acharya, P.; Chattopadhyaya, J. Stereoectronic Effects in Nucleosides and Nucleotides and Their Structural Implications, 2 nd ed.; Uppsala University Press: Uppsala, Sweden, 2005.
19. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344
20. de Leeuw, F. A. A. M.; Altona, C. J. Chem. Soc., Perkin Trans. 2 1982, 375-384
21. Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. J. Org. Chem. 1998, 63, 4967-4984
22. Martin-Pintado, N.; Deleavey, G. F.; Portella, G.; Campos-Olivas, R.; Orozco, M.; Damha, M. J.; Gonzalez, C. Angew. Chem., Int. Ed. 2013, 52, 12065-12068
23. Jenkins, I. D.; Verheyden, J. P. H.; Moffatt, J. G. J. Am. Chem. Soc. 1976, 98, 3346-3357
24. Ivanov, M. A.; Ludva, G. S.; Mukovnya, A. V.; Kochetkov, S. N.; Tunitskaya, V. L.; Alexandrova, L. A. Russ. J. Bioorg. Chem. 2010, 36, 488-496
25. Guillerm, D.; Muzard, M.; Allart, B.; Guillerm, G. Bioorg. Med. Chem. Lett. 1995, 5, 1455-1460
26. Owen, G. R.; Verheyden, J. P. H.; Moffatt, J. G. J. Org. Chem. 1976, 41, 3010-3017
27. Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783-2792
28. de Leeuw, F. A. A. M.; Van Beuzekom, A. A.; Altona, C. J. Comput. Chem. 1983, 4, 438-448
29. Hall, L. H.; Steiner, P. R.; Pedersen, C. Can. J. Chem. 1970, 48, 1155-1165
30. Hall, L. H.; Steiner, P. R.; Pedersen, C. Can. J. Chem. 1970, 48, 3937-3945
31. Inch, T. D. Annu. Rep. NMR Spectrosc. 1969, 2, 35-82
32. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
33. The pseudorotation angle for the minimized structure of 2′,4′-diF-araU was calculated using the online tool for pseudorotational analysis Prosit: http://cactus.nci.nih.gov/prosit/.
34. Seth, P. P.; Yu, J. H.; Jazayeri, A.; Pallan, P. S.; Allerson, C. R.; Ostergaard, M. E.; Liu, F. W.; Herdewijn, P.; Egli, M.; Swayze, E. E. J. Org. Chem. 2012, 77, 5074-5085
35. Noy, A.; Luque, F. J.; Orozco, M. J. Am. Chem. Soc. 2008, 130, 3486-3496
36. Noy, A.; Perez, A.; Marquez, M.; Luque, F. J.; Orozco, M. J. Am. Chem. Soc. 2005, 127, 4910-4920
37. Mangos, M. M.; Damha, M. J. Curr. Top. Med. Chem. 2002, 2, 1145-1169
38. Min, K. L.; Viazovkina, E.; Galarneau, A.; Parniak, M. A.; Damha, M. J. Bioorg. Med. Chem. Lett. 2002, 12, 2651-2654
39. Gong, Q. G.; Menon, L.; Ilina, T.; Miller, L. G.; Ahn, J.; Parniak, M. A.; Ishima, R. Chem. Biol. Drug Des. 2011, 77, 39-47