Total synthesis of the hypermodified RNA bases wybutosine and hydroxywybutosine and their quantification together with other modified RNA bases in plant materials

Chemistry - A European Journal

Volumn 19, Issue 13, 2013, Pages 4244-4248

  Hienzsch, Antje ^a   Deiml, Christian ^a   Reiter, Veronika ^a   Carell, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

isotopic labeling; liquid chromatography; natural products; nucleosides; RNA

Indexed keywords

ARABIDOPSIS THALIANA; EFFICIENT SYNTHESIS; INTRAMOLECULAR HYDROAMINATION; ISOTOPIC LABELING; ISOTOPICALLY LABELED; NATURAL PRODUCTS; NUCLEOSIDES; SUBSTITUTED SIDE CHAINS;

CHEMICAL PLANTS; ISOTOPES; LIQUID CHROMATOGRAPHY; SYNTHESIS (CHEMICAL); TISSUE;

RNA;

DRUG DERIVATIVE; GUANOSINE; NUCLEOSIDE; TRANSFER RNA; WYBUTOSINE;

ANIMAL; ARABIDOPSIS; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; MOUSE; NUCLEAR MAGNETIC RESONANCE; SWINE; SYNTHESIS;

ANIMALS; ARABIDOPSIS; CHROMATOGRAPHY, LIQUID; GUANOSINE; ISOTOPE LABELING; MICE; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; NUCLEOSIDES; RNA, TRANSFER; SWINE;

EID: 84875160429     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204209     Document Type: Article

References (35)

1. T. Carell, C. Brandmayr, A. Hienzsch, M. Müller, D. Pearson, V. Reiter, I. Thoma, P. Thumbs, M. Wagner, Angew. Chem. Int. Ed. 2012, 51, 7110-7131.
2. F. H. C. Crick, J. Mol. Biol. 1966, 19, 548-555
3. A. Maelicke, F. V. D. Haar, F. Cramer, Biopolymers 1973, 12, 27-43
4. L. S. Kan, P. O. P. Ts'o, F. Von der Haar, M. Sprinzl, F. Cramer, Biochemistry 1975, 14, 3278-3291.
5. A. L. Konevega, N. G. Soboleva, V. I. Makhno, Y. P. Semenikov, W. Wintermeyer, M. V. Rodnina, V. I. Katunin, RNA 2004, 10, 90-101.
6. V. Dao, R. Guenther, A. Malkiewicz, B. Nawrot, E. Sochacka, A. Kraszewski, J. Jankowska, K. Everett, P. F. Agris, Proc. Natl. Acad. Sci. USA 1994, 91, 2125-2129
7. D. R. Kearns, K. L. Wong, Y. P. Wong, Proc. Natl. Acad. Sci. USA 1973, 70, 3843-3846.
8. V. Katunin, N. Soboleva, V. Mahkno, E. Sedelnikova, S. Zhenodarova, S. Kirillov, Biochimie 1994, 76, 51-57.
9. R. Thiebe, H. G. Zachau, Eur. J. Biochem. 1968, 5, 546-555
10. G. Krauss, F. Peters, G. Maass, Nucl. Acids Res. 1976, 3, 631-640
11. W. Wintermeyer, H. G. Zachau, Eur. J. Biochem. 1979, 98, 465-475
12. D. W. Smith, A. L. McNamara, J. F. Mushinski, D. L. Hatfield, J. Biol. Chem. 1985, 260, 147-151.
13. W. F. Waas, Z. Druzina, M. Hanan, P. Schimmel, J. Biol. Chem. 2007, 282, 26026-26034.
14. B. A. Carlson, B. J. Lee, D. L. Hatfield, Biochem. Biophys. Res. Commun. 2008, 375, 86-90.
15. B. A. Carlson, J. F. Mushinski, D. W. Henderson, S. Y. Kwon, P. F. Crain, B. J. Lee, D. L. Hatfield, Virology 2001, 279, 130-135.
16. H. Bazin, X. X. Zhou, C. Glemarec, J. Chattopadhyaya, Tetrahedron Lett. 1987, 28, 3275-3278.
17. S.-i. Nakatsuka, T. Ohgi, T. Goto, Tetrahedron Lett. 1978, 19, 2579-2582.
18. T. Itaya, M. Morisue, M. Shimomichi, M. Ozasa, S. Shimizu, S. Nakagawa, J. Chem. Soc. Perkin Trans. 1 1994, 2759-2765.
19. D. M. Bartley, J. K. Coward, J. Org. Chem. 2005, 70, 6757-6774.
20. W. Dohle, D. M. Lindsay, P. Knochel, Org. Lett. 2001, 3, 2871-2873.
21. Y. Feng, J. K. Coward, J. Med. Chem. 2005, 48, 655.
22. C. Bonini, G. Righi, Tetrahedron 1992, 48, 1531-1538.
23. S. Porcher, Helv. Chim. Acta 2008, 91, 1219-1235.
24. C. Brandmayr, M. Wagner, T. Brückl, D. Globisch, D. Pearson, A. C. Kneuttinger, V. Reiter, A. Hienzsch, S. Koch, I. Thoma, P. Thumbs, S. Michalakis, M. Müller, M. Biel, T. Carell, Angew. Chem. Int. Ed. 2012, 51, 11162-11165.
25. P. Chen, G. Jager, B. Zheng, BMC Plant Biol. 2010, 10, 201.
26. L. Y. Atanasova, Compt. Rend. Acad. bulg. Sci. 2011, 64, 67-74.
27. L. Jones, T. Scott, Plant Physiol. 1981, 67, 535-538.
28. B. S. Vold, P. S. Sypherd, Proc. Natl. Acad. Sci. USA 1968, 59, 453-458
29. G. N. Brown, Plant Physiol. 1969, 44, 272-276.
30. K. E. Koch, Annu. Rev. Plant Physiol. Plant Mol. Biol. 1996, 47, 509-540.
31. L. Marechal-Drouard, J. H. Weil, A. Dietrich, Annu. Rev. Plant Physiol. Plant Mol. Biol. 1993, 44, 13-32.
32. G. R. Björk, J. Kohli, in Chromatography and Modification of Nucleosides: Biological roles and function of modification (Eds.:, C. W. Gehrke, K. C. T. Kuo,), Elsevier, Amsterdam, 1990, pp. 813-867.
33. H. Sakakibara, Annu. Rev. Plant Biol. 2006, 57, 431-449.
34. M. Allen, W. Qin, F. Moreau, B. Moffatt, Physiol. Plant. 2002, 115, 56-68
35. K. M. Schnorr, C. Gaillard, E. Biget, P. Nygaard, M. Laloue, Plant J. 1996, 9, 891-898.