2′-O-[2-(amino)-2-oxoethyl] oligonucleotides

Organic Letters

Volumn 5, Issue 4, 2003, Pages 403-406

  Prakash, Thazha P ^a   Kawasaki, Andrew M ^a   Lesnik, Elena A ^a   Owens, Stephen R ^a   Manoharan, Muthiah ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; COMPLEMENTARY RNA; NUCLEASE; NUCLEOSIDE DERIVATIVE; OLIGONUCLEOTIDE; RNA; ANTISENSE OLIGONUCLEOTIDE; PHOSPHODIESTERASE; PHOSPHODIESTERASE I;

ARTICLE; BINDING AFFINITY; CHEMICAL MODIFICATION; ENZYME STABILITY; GENE TARGETING; SYNTHESIS; CHEMISTRY; DRUG STABILITY; METABOLISM; STRUCTURE ACTIVITY RELATION;

DRUG STABILITY; OLIGONUCLEOTIDES, ANTISENSE; PHOSPHODIESTERASE I; PHOSPHORIC DIESTER HYDROLASES; RNA, COMPLEMENTARY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0038683620     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027131k     Document Type: Article

References (18)

1. (a) Cook P. D. In Antisense Medicnal Chemistry; Crooke, S. T., Ed.; Antisense Research and Application, Vol. 131; Springer-Verlag: New York, 1998; pp 51-101.
2. (b) Cook, P. D. Nucleosides Nucleotides 1999, 18, 1141-1162.
3. (c) Prakash, T. P.; Manoharan, M.; Fraser, A. S.; Kawasaki, A. M.; Lesnik, E. A.; Owens, S. R. Tetrahedron Lett. 2000, 41, 4855-4859 and references cited therein.
4. (a) Martin, P. Helv. Chim. Acta 1995, 78, 486-504
5. (b) Manoharan, M. Biochim. Biophys. Acta 1999, 1489, 117-130.
6. (c) Monia, B. P.; Lesnik, E. A.; Gonzalez, C.; Lima, W. F.; Guinosso, C. J.; Kawasaki, A. M.; Cook, P. D.; Freier, S. M. J. Biol. Chem. 1993, 268, 14514-14522.
7. Grotli, M.; Beijer, B.; Sproat, B. Tetrahedron 1999, 55, 4299-4314.
8. Wolfe, S. Acc. Chem. Res. 1972, 5, 102-111.
9. Teplova, M.; Minasov, G.; Tereshko, V.; Inamati, G. B.; Cook, P. D.; Manoharan, M.; Egli, M. Nat. Struct. Biol. 1999, 6, 535-539.
10. Cook, P. D.; Manoharan, M.; Guinosso, C. J. PCT International Application, Isis Pharmaceuticals, Inc., 1995.
11. Prakash, T. P.; Kawasaki, A. M.; Fraser, A. S.; Vasquez, G.; Manoharan, M. J. Org. Chem. 2002, 67, 357-369.
12. Reddy, M. P.; Farooqui, F.; Hanna, N. B. Tetrahedron Lett 1996, 37, 8691-8694.
13. Manoharan, M.; Lu, Y.; Casper, M. D.; Just, G. Org. Lett. 2000, 2, 243-246. Although CSO has been used for oxidation of internucleosidic phosphite groups, other conventional oxidizing agents such as tert-butyl hydroperoxide in acetonitrile or iodine in tetrahydrofuran, pyridine, and water may also be used.
14. (a) Keller, T. H.; Haner, R. Helv. Chim. Acta 1993, 76, 884-892.
15. (b) Keller, T. H.; Haner, R. Nucleic Acids Res. 1993, 21, 4499-4505.
16. Freier, S. M.; Altmann, K.-H. Nucleic Acids Res. 1997, 25, 4429-4443.
17. Griffey, R. H.; Monia, B. P.; Cummins, L. L.; Freier, S.; Greig, M. J.; Guinosso, C. J.; Lesnik, E.; Manalili, S. M.; Mohan, V.; Owens, S.; Ross, B. R. ; Sasmor, H.; Wancewicz, E.; Weiler, K.; Wheeler, P. D.; Cook, P. D. J. Med. Chem. 1996, 39, 5100-5109.
18. Cummins, L. L.; Owens, S. R.; Risen, L. M.; Lesnik, E. A.; Freier, S. M. ; McGee, D.; Guinosso, C. J.; Cook, P. D. Nucleic Acids. Res. 1995, 23, 2019-2024.