Oligonucleotide N3'→P5' thiophosphoramidates: Synthesis and properties

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7661-7664

  Pongracz, Krisztina ^a   Gryaznov, Sergei ^a  

^a GERON CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; MOLECULAR STABILITY; RNA BINDING; STRUCTURE ANALYSIS;

EID: 0033595857     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01584-1     Document Type: Article

References (11)

1. Roush, W. Science 1997, 276, 1192-1193.
2. DeMesmaeker, A.; Altman, K.-H.; Waldner, A.; Wendeborn, S. Current Opinion in Struct. Biol. 1995, 5, 343-355.
3. Gryaznov, S.; Chen J.-K. J. Am. Chem. Soc. 1994, 116, 3143-3144.
4. Chen, J.-K.; Schultz, R. G.; Lloyd, D. H.; Gryaznov, S. M. Nucl. Acids Res. 1995, 23, 2661-2668.
5. Gryaznov, S. M.; Lloyd, D. H.; Chen, J.-K.; Schultz, R. G.; DeDionisio, L. A.; Ratmeyer, L.; Wilson, W. D. Proc. Natl. Acad. Sci. USA 1995, 92, 5798-5802.
6. Skorski, T.; Perrotti, D.; Nieborowska-Skorska, M.; Gryaznov, S.; Calabretta, B. Proc. Natl. Acad. Sci. USA 1997, 94, 3966-3971.
7. Gryaznov, S. M.; Skorski, T.; Cucco, C; Nieborowska-Skorska, M.; Chiu, C.-Y.; Lloyd, D. H.; Chen, J.-K.; Koziolkiewicz, M.; Calabretta, B. Nucleic Acids Res. 1996, 24, 1508-1514.
8. Nelson, J. S.; Fearon, K. L.; Nguyen, M. Q.; McCurdy, S. N.; Frediani, J. F.; Foy, M. F.; Hirschbein, B. L. J. Org. Chem. 1997, 62, 7278-7287. The phosphoramidites were purchased from Cruachem and JBL Scientific.
9. Iyer, R. P.; Phillips, L. R.; Egan, W.; Regan, J. B.; Beaucage, S. L. J. Org. Chem. 1990, 55, 4693-4699.
10. 3N, 99/1, v/v as the sulfurizing agent on 1 μmole scale.
11. 2 calculated 3 577.11 and 4202.69, found by MALDI MS 3577 and 4203, respectively; mobility in 15% Page relative to isosequential phosphoramidates was 0.95 and 0.97, respectively.