Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

Tetrahedron Letters

Volumn 51, Issue 15, 2010, Pages 2036-2038

  Fujino, Tomoko ^a   Tsunaka, Nobuhide ^a   Guillot Nieckowski, Marine ^b   Nakanishi, Waka ^a   Iwamoto, Takeaki ^a   Nakamura, Eiichi ^b   Isobe, Hiroyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Artificial deoxyribonucleoside; Puckering conformation; Transglycosylation

Indexed keywords

ADENINE; CYTOSINE; DNA; GUANINE; TRIAZOLE DERIVATIVE;

ARTICLE; DNA DETERMINATION; DNA STRUCTURE; DNA SYNTHESIS; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 77649272463     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.046     Document Type: Article

References (16)

1. Saenger W. Principle of Nucleic Acid Structure (1984), Springer, New York
2. Isobe H., Fujino T., Yamazaki N., Guillot-Nieckowski M., and Nakamura E. Org. Lett. 10 (2008) 3729-3732
3. Fujino T., Yamazaki N., and Isobe H. Tetrahedron Lett. 50 (2009) 4101-4103
4. Imazawa M., and Eckstein F. J. Org. Chem. 43 (1978) 3044-3048
5. Vorbrüggen H., and Bennua B. Chem. Ber. 114 (1981) 1279-1286
6. 3SiOTf. Vorbrüggen H., Krolikiewicz K., and Bennua B. Chem. Ber. 114 (1981) 1234-1255
7. The reaction with guanine nucleophile gave two other transglycosylated products (ca. 4% yield, respectively) which are tentatively assigned as 7-glycosylated byproducts (Ref. 3). We did not observe similar isomeric byproducts with adenine nucleophile.
8. Van Roey P., Salerno J.M., Duax W.L., Chu C.K., Ahn M.K., and Schinazi R.F. J. Am. Chem. Soc. 110 (1988) 2277-2282
9. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68
10. max shows the degree of distortion of the ring from the planar form.
11. Observed phase angles of the analogues were in the range similar to the natural congeners (Ref. 1). See also:. Altona C., and Sundaralingam M. J. Am. Chem. Soc. 94 (1972) 8205-8212
12. Altona C., and Sundaralingam M. J. Am. Chem. Soc. 94 (1973) 8205-8212
13. Coupling analysis in aqueous solution was not successful due to low solubility of the analogues.
14. H3′,H4′)).
15. Mathé C., and Périgaud C. Eur. J. Org. Chem. (2008) 1489-1505
16. Sørensen M.H., Nielsen C., and Nielsen P. J. Org. Chem. 66 (2001) 4878-4886