Biopolym. Cell. 2001; 17(4):325-330.
Bioorganic Chemistry
Preparative synthesis and some properties of deoxyribosylurea, the product of DNA oxidative degradation
- Institute of Molecular Biology and Genetics, NAS of Ukraine
150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680
Abstract
An efficient method for the preparation of 2'-deoxyribosylurea is proposed that includes the oxidation of 5'-O-protected thymidine with potassium permanganate and alkaline hydrolysis of intermediate thymidine glycol. The possibility of detection of urea residues in oligonucleotides has been studied.
Full text: (PDF, in Ukrainian)
References
[1]
Knorre DG, Fedorova OS, Frolov EI. Oxidative degradation of nucleic acids. Uspekhi sovrem khimii. 1993; 62(1):70-91.
[2]
Pratviel G, Bernadou J, Meunier B. Carbon—hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs. Angew Chem Int Ed Engl. 1995;34(7):746–69.
[3]
Burrows CJ, Muller JG. Oxidative nucleobase modifications leading to strand scission. Chem Rev. 1998;98(3):1109-1152.
[4]
Jones AS, Ross GW, Takemura S, Thompson TW, Walker RT. 66. The nucleotide sequence in deoxyribonucleic acids. Part VI. The preparation and reactions of permanganate-oxidised deoxyribonucleic acid. J Chem Soc. 1964;373-8.
[5]
Goody RS, Jones AS, Walker RT. The permanganate oxidation of cytosine derivatives. Tetrahedron. 1971;27(1):65–9.
[6]
Iida S, Hayatsu H. The permanganate oxidation of thymidine and thymidylic acid. Biochim Biophys Acta. 1971;228(1):1-8.
[7]
Iida S, Hayatsu H. The permanganate oxidation of deoxyribonucleic acid. Biochim Biophys Acta. 1971;240(3):370–5.
[8]
Howgate P, Jones AS, Tittensor JR. The permanganate oxidation of thymidine. J Chem Soc. 1968;275-9.
[9]
Breimer L, Lindahl T. A DNA glycosylase from Escherichia coli that releases free urea from a polydeoxyribonucleotide containing fragments of base residues. Nucleic Acids Res. 1980;8(24):6199-211.
[10]
Cadet J, Teoule R. Chimie des acides nucleiques. I. Oxydation permanganique de la thymidine en solution aqueuse a pH 3,9. Bull Soc Chim F r. 1974;(7-8):1565-70 .
[11]
Cadet J, Teoule R. Radiolyse gamma de la thymidine en solution aqueuse aeree. II. Characterisation des produits stables. Bull Soc Chim F r. 1975; (3-4): 885-90.
[12]
Benn MH, Jones AS. Glycosylureas. Part I. Preparation and some reactions of D-glucosylureas and D-ribosylureas. J Chem Soc. 1960;3837-41.
[13]
Jensen WE, Jones AS, Ross GW. Glycosylureas. Part II. The synthesis and properties of 2-deoxy-D-ribosylureas. J Chem Soc. 1965;2463-5.
[14]
Guy A, Ahmad S, T?oule R. Insertion of the fragile 2?-deoxyribosylurea residue into oligodeoxynucleotides. Tetrahedron Lett. 1990;31(40):5745–8.
[15]
Baillet S, Behr J-P. Deoxyribosylurea and deoxyribosylformamide oligonucleotides. Tetrahedron Lett. 1995;36(49):8981–4.
[16]
K?ster H, Hoppe N, Kohli V, Kr?pelin M, Kaut H, Kulikowski K. Some improvements in the synthesis of DNA of biological interest. Nucleic Acids Symp Ser. 1980;(7):39-60.
[17]
Hubener Hj, Bode F, Mollat Hj, Wehner M. [Quantitative determination of urea in paper chromatogram]. Hoppe Seylers Z Physiol Chem. 1952;290(3-6):136-8.
[18]
Schaller H, Weimann G, Lerch B, Khorana HG. Studies on Polynucleotides. XXIV. 1 The Stepwise Synthesis of Specific Deoxyribopolynucleotides (4). 2 Protected Derivatives of Deoxyribonucleosides and New Syntheses of Deoxyribonucleoside-3? Phosphates 3 . J Am Chem Soc. 1963;85(23):3821–7.
[19]
Kow YW, Wallace SS. Exonuclease III recognizes urea residues in oxidized DNA. Proc Natl Acad Sci U S A. 1985;82(24):8354-8.
[20]
Ide H, Melamede RJ, Wallace SS. Synthesis of dihydrothymidine and thymidine glycol 5'-triphosphates and their ability to serve as substrates for Escherichia coli DNA polymerase I. Biochemistry. 1987;26(3):964-9.
[21]
Guy A, Duplaa AM, Ulrich J, T?oule R. Incorporation by chemical synthesis and characterization of deoxyribosylformylamine into DNA. Nucleic Acids Res. 1991;19(21):5815-20.
[22]
Lemieux RU. The configuration and conformation of thymidine. Can J Chem. 1961; 39(1): 116-120.
[23]
Robins MJ, Robins RK. Purine nucleosides. XI. The synthesis of 2'-deoxy-9-alpha- and-beta-D-ribofuranosylpurines and the correlation of their anomeric structure with proton magnetic resonance spectra. J Am Chem Soc. 1965;87(21):4934-40.
[24]
Cleve G, Hoyer G-A, Schulz G, Vorbr?ggen H. Nucleosidsynthesen, VIII. NMR- und CD-Spektren von Pyrimidin-nucleosiden und ihren 2-Thioanaloga. Chem Ber. 1973;106(9):3062–72.
[25]
Wheeler DD, Young DC, Erley DS. Reactions of phthalaldehydic acid. J Org Chem. 1957;22(5):547–56.