Synthesis of functionally modified oligonucleotides from methoxyoxalamido precursors

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3231-3234

  Polushin, Nikolai N ^a  

^a PERKINELMER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYURIDINE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0029998782     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00537-0     Document Type: Article

References (19)

1. The results of this work were presented at the Nucleic Acids Symposium: 6-11 August, 1995, Noordwijkerhout, the Netherlands.
2. Goodchild, J. Conjugates of Oligonucleotides and Modified Oligonucleotides: A Review of Their Synthesis and Properties. In Perspectives in Bioconjugate Chemistry; Meares, C.F. Ed.; ACS, Washington, DC, 1993, pp. 77-99, and references cited therein.
3. Ferentz, A.E.; Verdine, G.L. Nucleosides & Nucleotides. 1992, 11, 1749-1763.
4. Phosphodiester 6f was stable in 0.5 M methanolic KOH for at least 6 hrs at room temperature and in saturated aqueous ammonia for at least 16 hr at 55°C.
5. Alul, R.H.; Singman, C.N.; Zhang, G.; Letsinger, R.L. Nucl. Acids Res. 1991, 19, 1527-1532.
6. 2-2'-dU see: Polushin, N.N.; Smirnov I.P.; Verentchikov A.N.; Coull, J.M. Tetrahedron Lett. 1996, in press, and references cited therein.
7. 3CN (0.45 M, 1.2 eq, Activator Solution, DNA Synthesis Reagent, PerSeptive Biosystems) were consecutively added with stirring methyl oxalyl chloride (1 eq, Aldrich) and 2,4,6-collidine (1 eq, Fluka). After 30 min the reaction mixture was centrifuged and the supernatant was used for the methoxyoxalylation reaction.
8. 2-5').
9. Polushin, N.N.; Chen, B-c.; Anderson, L.W.; Cohen, J.S. J. Org. Chem. 1993, 58, 4606-4613.
10. +), calc. M = 831.32.
11. 5'-HO-T-3'-DMT was purchased from Glen Research.
12. Oxidizer Solution, DNA Synthesis Reagent, PerSeptive Biosystems.
13. 31P-NMR (200 MHz, DMSO-d6): upper isomer: δ -2.38, lower isomer: δ -1.58.
14. - = 616.19;
15. +), calc. M= 616.22;
16. +), calc. M= 660.24;
17. +), calc. M= 799.42.
18. 10 (DAD)).
19. Smirnov, I.P.; Roskey, M.T.; Juhasz, P.; Takach, E.J.; Martin, S.A.; Haff, L.A. Submitted to Anal. Biochem, 1996