Synthesis of oligonucleotides containing 2'-azido-and 2'-amino-2'-deoxyuridine using phosphotriester chemistry

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3227-3230

  Polushin, Nikolai N ^a   Smirnov, Igor P ^a   Verentchikov, Anatoli N ^a   Coull, James M ^a  

^a PERKINELMER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYURIDINE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029998781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00536-9     Document Type: Article

References (13)

1. The results of this work were presented at the Nucleic Acids Symposium: 6-11 August, 1995, Noordwijkerhout, the Netherlands.
2. Sanghvi, Y.S.; Cook, P.D. In Sanghvi, Y.S. and Cook, P.D (eds) Carbohydrate Modifications in Antisense Research, ACS Symposium Series N° 580, ACS, Washington, DC, 1994; pp. 9-11, and references cited therein.
3. Shchepinov, M.S.; Korobko, V.G.; Dobrynin, V.N. Miami Bio/Technology European Symposium, Monte-carlo, Monaco, November, 1994, poster Su 49a.
4. Efimov, V.A.; Buryakova, A.A.; Dubey, I.Y., Polushin, N.N.; Chakhmakhcheva, O.G; Ovchinnikov, Yu. A. Nucl. Acids Res. 1986, 14, 6525-6540.
5. 3-2'-dU see: Verheyden, J.P.H., Wagner, D., Moffatt, J.G. J. Org. Chem. 1971, 36, 250-254.
6. 3NH)).
7. 5'-HO-T-3'-DMT was purchased from Glen Research.
8. 2 was necessary to obtain a homogeneous solution.
9. Smirnov, I.P.; Roskey, M.T.; Juhasz, P.; Takach, E.J., Martin, S.A.; Haff, L.A. Submitted to Anal. Biochem, 1996.
10. Efimov, V.A.; Chakhmakhcheva, O.G.; Dubey, I.Y., Polushin, N.N. Nucl. Acids Res. Symp.Ser. 1987, 18, 213-216.
11. 31P-NMR (200 Mhz, DMSO-d6): δ -1.53 (d).
12. TCEP HCl is available from Pierce Chemical, Rockford, IL USA.
13. 31P-NMR (200 MHz, DMSO-d6); δ 0.20 (s). These data are identical to that from a separate sample prepared by coupling of 5'-DMT-2'-NHAc-2'-dU cyanoethyl phosphoramidite with 5'-HO-T-3'-DMT followed by oxidation and ammonia deprotection.