Abstract
acp3U is a hypermodified base that is found in the tRNAs of prokaryotes and eukaryotes and also in the ribosomal RNA of mammals. Its function has so far been unknown but it is speculated that acp3U complexes Mg ions, which may contribute to the stabilization of the RNA structure. As a hypermodified base in which a nucleoside is covalently connected to an amino acid, acp3U is a natural nucleoside between genotype and phenotype and hence is also of particular importance for theories about the origin of life. Herein, we report the development of a phosphoramidite building block and of a solid phase protocol that allows synthesis of RNA containing acp3U.
Dokumententyp: | Zeitschriftenartikel |
---|---|
EU Funded Grant Agreement Number: | 741912 |
EU-Projekte: | Horizon 2020 > ERC Grants > ERC Advanced Grant > ERC Grant 741912: EPiR - The Chemical Basis of RNA Epigenetics |
Publikationsform: | Postprint |
Fakultät: | Chemie und Pharmazie > Department Chemie |
Fakultätsübergreifende Einrichtungen: | Center for Integrated Protein Science Munich (CIPSM) |
Themengebiete: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
URN: | urn:nbn:de:bvb:19-epub-71481-0 |
ISSN: | 0009-241X; 0022-4936; 1359-7345; 1364-548X |
Sprache: | Englisch |
Dokumenten ID: | 71481 |
Datum der Veröffentlichung auf Open Access LMU: | 01. Apr. 2020, 11:30 |
Letzte Änderungen: | 18. Mai 2021, 12:45 |
Literaturliste: | 1 M. A. Machnicka, K. Milanowska, O. O. Oglou, E. Purta, M. Kurkowska, A. Olchowik, W. Januszewski, S. Kalinowski, S. Dunin-Howkawicz, K. M. Rother, M. Helm, J. M. Bujnicki, H. Grosjean, Nucleic Acids Res., 2013, 41, D262–D267. 2 W. V. Gilbert, T. A. Bell and C. Schaening, Science, 2016, 352, 14018–1412. 3 B. S. Zhao, I. A. Roundtree and C. He, Nat. Rew. Mol. Cell Biol., 2017, 18, 31–42. 4 S. R. Jaffrey, Nat. Struct. Mol. Biol., 2014, 21, 945–946. 5 E. M. Harcourt, A. M. Kietrys and E. T. Kool, Nature, 2017, 541, 339–346. 6 M. T. Wattsa and I. Tinoco, Biochemistry, 1978, 17, 2455–2463. 7 C. Schneider, S. Becker, H. Okamura, A. Crisp, T. Amatov, M. Stadlmeier and T. Carell, Angew. Chem., Int. Ed., 2018, 57, 5943–5946. 8 M. Di Giulio, J. Theor. Biol., 1998, 191, 191–196. 9 H. Grosjean, V. de Crecy-Lagard and G. R. Björk, Trends Biochem. Sci., 2004, 29, 519–522. 10 E. Szathmary, Trends Genet., 1999, 15, 223-229. 11 P. Gaytan, J. Yanez, F. Sanchez, H. Mackie and X. Soberon, Chem Biol., 1998, 5, 519–527. 12 H. Schirmeister-Tichy, G. G. Alvarado and W. Pfleiderer, Nucleos. Nucleot., 1999, 18, 1219–1220. 13 F. Himmelsbach, B. S. Schulz, T. Trichtinger, R. Charubala and W. Pfleiderer, Tetrahedron, 1984, 40, 59–72. 14 A. J. Ozinskas and G. A. Rosenthal, J. Org. Chem., 1986, 51, 5047–5050. 15 W. H. Dent III, W. R. Erickson, S. C. Fields, M. H. Parker and E. G. Tromiczak, Org. Lett., 2002, 4, 1249–1251. 16 C. Chaix, A. M. Duplaa, D. Molko and R. Teoule, Nucleic Acids Res., 1989, 17, 7381–7393. 17 J. Stawinski, R. Strömberg, M. Thelin and E. Westman, Nucleic Acids Res., 1988, 16, 9285–9298. 18 S. M. Ching, W. J. Tan, K. L. Chua and Y. Lam, Bioorg. Med. Chem., 2010, 18, 6657–6665. 19 M. de Champdore, L. De Napoli, G. Di Fabio, A. Messere, D. Montesarchio and G. Piccialli, J. Chem. Soc. Chem. Commun., 2001, 2598-2599. 20 B. M. Trost and C. G. Caldwell, Tetrahedron Lett., 1981, 22, 4999–5002 21 M. Sekine, S. Limura and K. Furusawa, J. Org. Chem., 1993, 58, 3204–3208. 22 H. Schaller, G. Weimann, B. Lerch and H. G. Khorana, J. Am. Chem. Soc., 1963, 85, 3821–3827. 23 K. L. Agarwal, A. Yamazaki, P. J. Cashion and H. G. Khorana, Angew. Chem., Int. Ed. Engl., 1972, 11, 451–459. 24 N. Usman, K. K. Ogilvie, M. Y. Jiang and R. J. Cedergren, J. Am. Chem. Soc., 1987, 109, 7845–7854. 25 H. Seliger, D. Zeh, G. Azuru and J. B. Chattopadhyaya, Chem. Scr., 1983, 22, 95–102. 26 M. H. Caruthers, D. Dellinger, K. Prosser, A. D. Brone, J. W. Dubendorff, R. Kierzek and M. Rosendahl, Chem. Scr., 1986, 26, 25–30. 27 R. Kierzek, M. H. Caruthers, C. E. Longfellow, D. Swinton, D. H. Turner and S. M. Freier, Biochemistry, 1986, 25, 7840–7846. 28 I. Hirao, M. Ishikawa and K. Miura, Nucleic Acids Symp. Ser., 1985, 16, 173-176. 29 H. Tanimura, T. Fukuzawa, M. Sekine, T. Hata, J. W. Efcavitch and G. Zon, Tetrahedron Lett., 1988, 29, 577–578. 30 H. Tanimura, M. Sekine and T. Hata, Nucleos. Nucleot., 1986, 5, 363–383. 31 H. Tanimura and T. Imada, Chem. Lett., 1990, 1715–1718. |