Synthesis of 8-oxo-7,8-dihydro-6-O-methyl-2′-deoxyguanosine and its use as a probe to study DNA-base excision by mutY enzyme

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 9-12

  Varaprasad, Chamakura V ^a   Bulychev, Nickolai ^a   Grollman, Arthur P ^a   Johnson, Francis ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXY 7,8 DIHYDRO 8 OXOGUANOSINE; DEOXYGUANOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA DAMAGE; DRUG SYNTHESIS; GENETIC ANALYSIS; MUTATION; TECHNIQUE;

EID: 0030049828     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02069-1     Document Type: Article

References (16)

1. Michaels, M.L. ; Tchou, J. ; Grollman, A.P. ; Miller, J.H. Biochemistry 1992, 31, 10964-10968 .
2. Tchou, J. ; Bodepudi, V. ; Shibutani, S. ; Antoshechkin, I. ; Miller, J. ; Grollman, A.P. ; Johnson, F. J Biol. Chem. 1994, 269 (21), 15318-15324.
3. The compound 1 (92% yield) was obtained from its PAC-derivative 10 by its treatment with ethanolic methyl amine (33%) for 4h at 24°C. Interestingly no displacement of the 6-O-methyl group was observed when the monomer 10 treated with methyl amine or ammonia under the conditions of DNA synthesis in contrast to such substitution which occurs with 6-O-memyl dG.
4. 2O requires C, 43.91; H, 5.16; N, 23.28 %). M. p. 191°C.
5. Bodepudi, V. ; Shibutani, S. ; Johnson, F. Chem. Res. Toxicology 1992, 5, 608-617.
6. Schulhof, J.C. ; Moko, D. ; Teoule, R. Nucleic Acids Research 1987, 15, 397-416.
7. a) Mitsnobu, O. Synthesis 1981, 1-28.
8. b) Himmelsbach, F. ; Schulz, B.S. ; Trichtinger, T. ; Charubala, R. ; Pfleiderer, W. Tetrahedron 1984, 40 (1), 59-72.
9. c) Khazanchi, R. ; Yu, P-L. ; Johnson, F. J. Org. Chem 1993, 58, 2552-2556.
10. 31P and FAB-MS) data.
11. Bodepudi, V. ; Iden, C.R. ; Johnson, F. Nucleosides and Nucleotides 1991, 10(4), 755-761.
12. a) Beaucage, S.L. in Methods in Molecular Biology, 20, pp33: Protocols for Oligonucleotides and Analogs, Ed. Agrawal, S. (1993), Humana Press Inc., Totowa, NJ, USA.
13. a) Beaucage, S.L. in Methods in Molecular Biology, 20, pp33: Protocols for Oligonucleotides and Analogs, Ed. Agrawal, S. (1993), Humana Press Inc., Totowa, NJ, USA.
14. b) Monomer 10 was found to be stable to the reagents used for DNA synthesis.
15. Kuchino, Y. ; Mori, F. ; Kasai, H. ; Inoue, H. ; Iwai, S. ; Miura, K. ; Ohtsuka, E. ; Nishimura, S. Nature 1987, 327 (7), 77-79.
16. For a complete discussion of the biological data see Bulychev, N. ; Varaprasad, V. C. ; Johnson, F. ; Grollman, A. P. J. Biol. Chem. (submitted for publication).