Site-specific 15N-labelling of Adenine in DNA for NMR Studies

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 10, 1996, Pages 1179-1182

  Xu, Yao Zhong ^a   Ramesh, Vasudevan ^b   Swann, Peter F ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

6 MERCAPTOPURINE DERIVATIVE; ADENINE; AMMONIA; HYPOXANTHINE; NITROGEN 15; OLIGODEOXYNUCLEOTIDE; SYNTHETIC DNA;

ARTICLE; DNA SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; NUCLEAR MAGNETIC RESONANCE;

EID: 0030005419     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00194-1     Document Type: Article

References (25)

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19. The work was presented as a poster at 11th International Round Table Nucleosides, Nucleotides and Their Biological Applications in Leuven Belgium in Sept. 1994 (see, Xu, Y.-Z.; Zheng, Q. and Swann, P.F. Nucleosides and Nucleotides 1995 14, 929-932).
20. Early work on utilization of oxidized methylthiopurine in nucleosides: a) Wetzel, R. and Eckstein, F. J. Org. Chem. 1975 40, 658-660;
21. b) Seela, F.; Herdering, W. and Kehne, A. Helv. Chim. Acta 1987 70 1649-1660. On the oligonucleotide level, the oxidized methylthiopurine was used as a precursor to N6,N6-ethynoadenine in a polythymine
22. [c) Matteucci, M.D. and Webb, T.R. Tetrahedron Lett. 1987 28 2469-2472] and to 6-pyridium-purine
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24. The pentamer containing 6-methylthiopurine was treated with 5 ml of 1% MCPBA for 5 min and then with cone, aqueous ammonia at RT for 3 days. The transformed pentamer (containing adenine) was obtained in high yield, virtually the same as that of normal pentamer, and confirmed by nucleoside composition analysis.
25. The substitution of the oxidized pentamer with 2 M ammonia in methanol at RT overnight gave oligomer containing 6-methoxypurine as the major product with no (or little) amount of hydrolysed product when cone, aqueous ammonia (or 0.5 M NaOH) was employed at RT for 2 days for deprotection. However, the treatment with 0.5 M NaOH at RT for 3 days for the substitution and deprotection gave the hydrolysed product only. These experiments suggested the substitution is faster than the deprotection.