A convenient synthesis of 5-hydroxy-2'-deoxycytidine phosphoramidite and its incorporation into oligonucleotides

Tetrahedron Letters

Volumn 38, Issue 43, 1997, Pages 7531-7534

  Romieu, Anthony ^a   Gasparutto, Didier ^a   Molko, Didier ^a   Cadet, Jean ^a  

^a CEA GRENOBLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE DERIVATIVE; OLIGONUCLEOTIDE;

ARTICLE; DNA SYNTHESIS; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0030861036     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10024-7     Document Type: Article

References (15)

1. von Sonntag, C. ; Schuchmann, H.P. Int. J. Radiat. Biol. 1986, 49, 1-34. Decarroz, C. ; Wagner, J.R. ; Cadet, J. Free Rad. Res. Comms. 1987, 2, 295-301. Wagner, J.R. ; Hum, C.C. ; Ames, B.N. Proc. Natl. Acad. Sci. USA 1992, 89, 3380-3384. Cadet, J. ; Berger, M. ; Douki, T. ; Ravanat, J.L. Rev. Physiol. Biochem. Pharmacol. 1997, 131, 1-87.
2. von Sonntag, C. ; Schuchmann, H.P. Int. J. Radiat. Biol. 1986, 49, 1-34. Decarroz, C. ; Wagner, J.R. ; Cadet, J. Free Rad. Res. Comms. 1987, 2, 295-301. Wagner, J.R. ; Hum, C.C. ; Ames, B.N. Proc. Natl. Acad. Sci. USA 1992, 89, 3380-3384. Cadet, J. ; Berger, M. ; Douki, T. ; Ravanat, J.L. Rev. Physiol. Biochem. Pharmacol. 1997, 131, 1-87.
3. von Sonntag, C. ; Schuchmann, H.P. Int. J. Radiat. Biol. 1986, 49, 1-34. Decarroz, C. ; Wagner, J.R. ; Cadet, J. Free Rad. Res. Comms. 1987, 2, 295-301. Wagner, J.R. ; Hum, C.C. ; Ames, B.N. Proc. Natl. Acad. Sci. USA 1992, 89, 3380-3384. Cadet, J. ; Berger, M. ; Douki, T. ; Ravanat, J.L. Rev. Physiol. Biochem. Pharmacol. 1997, 131, 1-87.
4. von Sonntag, C. ; Schuchmann, H.P. Int. J. Radiat. Biol. 1986, 49, 1-34. Decarroz, C. ; Wagner, J.R. ; Cadet, J. Free Rad. Res. Comms. 1987, 2, 295-301. Wagner, J.R. ; Hum, C.C. ; Ames, B.N. Proc. Natl. Acad. Sci. USA 1992, 89, 3380-3384. Cadet, J. ; Berger, M. ; Douki, T. ; Ravanat, J.L. Rev. Physiol. Biochem. Pharmacol. 1997, 131, 1-87.
5. For the incorporation of 2 by enzymatic approach, see : Hatahet, Z. ; Purmal, A.A. ; Wallace, S.S. Nucleic Acids Res. 1993, 21, 1563-1568. Purmal, A.A. ; Wah Kow, Y. ; Wallace, S.S. Nucleic Acids Res. 1994, 22, 72-78.
6. For the incorporation of 2 by enzymatic approach, see : Hatahet, Z. ; Purmal, A.A. ; Wallace, S.S. Nucleic Acids Res. 1993, 21, 1563-1568. Purmal, A.A. ; Wah Kow, Y. ; Wallace, S.S. Nucleic Acids Res. 1994, 22, 72-78.
7. 18 column, 4.6×250 mm) with aq. triethylammonium acetate (TEAA, 25mM, pH = 7) as the eluent.
8. Schuloff J.C., Molko D., Téoule R. Nucleic Acids Res. 15:1987;397-415.
9. Eaton M.A., Hutchinson D.W. Biochim. Biophys. Acta. 319:1973;281-287.
10. Marchiewicz, W.T. J. Chem. Res. (S) 1979, 24-25.
11. +.
12. Gasparutto D., Livache T., Bazin H., Duplaa A.M., Guy A., Khorlin A., Molko D., Roget A., Téoule R. Nucleic Acids Res. 20:1992;5159-5166.
13. +.
14. The crude 5′-DMTr-oligomers were purified by reverse phase HPLC (Hamilton PRP3 column (polymeric phase) 10μ, 7×305 mm) with acetonitrile and TEAA as eluents using a non-linear gradient {100% TEAA, 25mM, pH = 7, (5 min), then isocratic TEAA/acetonitrile 92 8 (10 min)} ; in order to remove the DMTr group, the oligomers were treated with a solution of trifluoroacetic acid and water (TFA 1%) {isocratic 100% TFA(1%) (6 min)}. The resulting deprotected oligomers were again purified using the same eluents {gradient from 2 to 10% of acetonitrile (24 min)}.
15. Several 5-OHdC-containing oligonucleotides including a 22 mer are in preparation.