New RNA purine building blocks, 4'-selenopurine nucleosides: First synthesis and unusual mixture of sugar puckerings

Chemistry - A European Journal

Volumn 19, Issue 18, 2013, Pages 5528-5532

  Yu, Jinha ^a   Kim, Jin Hee ^a   Lee, Hyuk Woo ^a   Alexander, Varughese ^a   Ahn, Hee Chul ^b   Choi, Won Jun ^a   Choi, Jungwon ^c   Jeong, Lak Shin ^a  

^a Ewha Womans University   (South Korea)

^b Dongguk University   (South Korea)

^c Suwon University   (South Korea)

Author keywords

nucleic acids; nucleosides; RNA; selenonucleosides; X ray crystallography

Indexed keywords

BUILDING BLOCKES; D-RIBOSE; NUCLEOSIDES; PUCKERINGS; SELENONUCLEOSIDES;

BIOMOLECULES; NUCLEIC ACIDS; SELF ASSEMBLY; X RAY CRYSTALLOGRAPHY;

RNA;

4' SELENOADENOSINE; 4' SELENOGUANOSINE; 4'-SELENOADENOSINE; 4'-SELENOGUANOSINE; ADENOSINE; DRUG DERIVATIVE; GUANOSINE; NUCLEOSIDE; ORGANOSELENIUM DERIVATIVE; PURINE DERIVATIVE; RIBOSE; RNA;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ADENOSINE; CRYSTALLOGRAPHY, X-RAY; GUANOSINE; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEOSIDES; ORGANOSELENIUM COMPOUNDS; PURINES; RIBOSE; RNA; STEREOISOMERISM;

EID: 84876892147     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201300741     Document Type: Article

References (21)

1. R. T. Walker, E. De Clercq, F. Eckstein, in Nucleoside Analogues: Chemistry, Biology, and Medical Applications (Eds.:, R.T. Walker, E. DeClercq, F. Eckstein,), Plenum, New York, 1979, pp. 1-459.
2. M. Nasr, C. Litterst, J. McGowan, Antiviral Res. 1990, 14, 125-148.
3. P. Gunaga, H. R. Moon, W. J. Choi, D. H. Shin, J. G. Park, L. S. Jeong, Curr. Med. Chem. 2004, 11, 2585-2637.
4. A. Piperno, M. A. Chiacchio, D. Iannazzo, R. Romeo, Curr. Med. Chem. 2006, 13, 3675-3695
5. M. Ferrero, V. Gotor, Chem. Rev. 2000, 100, 4319-4348
6. J. A. Lee, L. S. Jeong, Antiviral Chem. Chemother. 2004, 15, 235-250
7. V. E. Marquez, M.-I. Lim, Med. Res. Rev. 1986, 6, 1-40.
8. L. S. Jeong, D. K. Tosh, H. O. Kim, T. Wang, X. Hou, H. S. Yun, Y. Kwon, S. K. Lee, J. Choi, L. X. Zhao, Org. Lett. 2008, 10, 209-212
9. V. Alexander, W. J. Choi, J. Chun, H. O. Kim, J. H. Jeon, D. K. Tosh, H. W. Lee, G. Chandra, J. Choi, L. S. Jeong, Org. Lett. 2010, 12, 2242-2245
10. K. Jayakanthan, B. D. Johnston, B. M. Pinto, Carbohydr. Res. 2008, 343, 1790-1800
11. J. K. Watts, B. D. Johnston, K. Jayakanthan, A. S. Wahba, B. M. Pinto, M. J. Damha, J. Am. Chem. Soc. 2008, 130, 8578-8579.
12. H. Vorbrüggen, C. Ruh-Polenz, Org. React. 2000, 55, 1-162
13. H. Vorbrüggen, K. Krolikiewicz, B. Bennua, Chem. Ber. 1981, 114, 1234-1255.
14. H. O. Kim, R. F. Schinazi, S. Nampalli, K. Shanmuganathan, D. L. Cannon, A. J. Alves, L. S. Jeong, J. W. Beach, C. K. Chu, J. Med. Chem. 1993, 36, 30-37
15. L. S. Jeong, R. F. Schinazi, J. W. Beach, H. O. Kim, S. Nampalli, K. Shanmuganathan, A. J. Alves, A. McMillan, C. K. Chu, J. Med. Chem. 1993, 36, 181-195.
16. T. Naka, N. Minakawa, H. Abe, D. Kaga, A. Matsuda, J. Am. Chem. Soc. 2000, 122, 7233-7243.
17. H. Batra, R. M. Moriarty, R. Penmasta, V. Sharma, G. Stanciuc, J. P. Staszewski, S. M. Tuladhar, D. A. Walsh, Org. Process Res. Dev. 2006, 10, 484-486.
18. G. Y. Song, V. Paul, H. Choo, J. Morrey, R. N. Sidewell, R. F. Schinazi, C. K. Chu, J. Med. Chem. 2001, 44, 3985-3993.
19. IUPAC-IUB Joint Commission on Biochemical Nomenclature, Eur. J. Biochem. 1983, 131, 9-15.
20. H. S. Shieh, H. M. Berman, Acta Crystallogr. B 1982, 38, 1513-1517
21. T. Ishida, A. Tanaka, M. Inuoe, T. Fujiwara, K. Tomita, J. Am. Chem. Soc. 1982, 104, 7239-7248.