Non-Hydrolyzable RNA–Peptide Conjugates: A Powerful Advance in the Synthesis of Mimics for 3′-Peptidyl tRNA Termini†
Holger Moroder
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorJessica Steger
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorDagmar Graber
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorKatja Fauster
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorKrista Trappl
Innsbruck Biocenter, Medical University of Innsbruck, Divison of Genomics and RNomics, 6020 Innsbruck (Austria)
Search for more papers by this authorViter Marquez Dr.
Gene Center, Department for Chemistry and Biochemistry and Center for Integrated Protein Science (CiPS-M), Ludwig-Maximillians-Universität, 81377 Munich (Germany)
Search for more papers by this authorNorbert Polacek Priv.-Doz. Dr.
Innsbruck Biocenter, Medical University of Innsbruck, Divison of Genomics and RNomics, 6020 Innsbruck (Austria)
Search for more papers by this authorDaniel N. Wilson Dr.
Gene Center, Department for Chemistry and Biochemistry and Center for Integrated Protein Science (CiPS-M), Ludwig-Maximillians-Universität, 81377 Munich (Germany)
Search for more papers by this authorRonald Micura Prof. Dr.
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorHolger Moroder
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorJessica Steger
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorDagmar Graber
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorKatja Fauster
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorKrista Trappl
Innsbruck Biocenter, Medical University of Innsbruck, Divison of Genomics and RNomics, 6020 Innsbruck (Austria)
Search for more papers by this authorViter Marquez Dr.
Gene Center, Department for Chemistry and Biochemistry and Center for Integrated Protein Science (CiPS-M), Ludwig-Maximillians-Universität, 81377 Munich (Germany)
Search for more papers by this authorNorbert Polacek Priv.-Doz. Dr.
Innsbruck Biocenter, Medical University of Innsbruck, Divison of Genomics and RNomics, 6020 Innsbruck (Austria)
Search for more papers by this authorDaniel N. Wilson Dr.
Gene Center, Department for Chemistry and Biochemistry and Center for Integrated Protein Science (CiPS-M), Ludwig-Maximillians-Universität, 81377 Munich (Germany)
Search for more papers by this authorRonald Micura Prof. Dr.
Institute of Organic Chemistry, Center for Molecular Biosciences CMBI, University of Innsbruck, 6020 Innsbruck (Austria), Fax: (+43) 507-512-2892
Search for more papers by this authorH. Moroder and J. Steger contributed equally to this work. Funding by the Austrian Science Foundation FWF (P17864 to R.M.; Y315 to N.P.) and the Ministry of Science and Research (GenAU project consortium “non-coding RNAs” P0726-012-012 to R.M. and D1042-011-011 to N.P) and the Deutsche Forschungsgemeinschaft DFG (WI3285/1-1 to D.N.W.) is acknowledged.
Graphical Abstract
Translation of specific small peptides on the ribosome can confer resistance to macrolide antibiotics. To reveal the molecular details of this and related phenomena, stable RNA–peptide conjugates that mimic peptidyl-tRNA would be desirable, especially for ribosome structural biology. A flexible solid-phase synthesis strategy now allows efficient access to these highly requested derivatives without restriction on the RNA and peptide sequences.
Abstract
Translation of specific small peptides on the ribosome can confer resistance to macrolide antibiotics. To reveal the molecular details of this and related phenomena, stable RNA–peptide conjugates that mimic peptidyl-tRNA would be desirable, especially for ribosome structural biology. A flexible solid-phase synthesis strategy now allows efficient access to these highly requested derivatives without restriction on the RNA and peptide sequences.
Supporting Information
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References
- 1
- 1aA. S. Mankin, Curr. Opin. Microbiol. 2008, 11, 414–421;
- 1bT. Tenson, A. S. Mankin, Mol. Microbiol. 2006, 59, 1664–1677;
- 1cV. Vimberg, L. Xiong, M. Bailey, T. Tenson, A. S. Mankin, Mol. Microbiol. 2004, 54, 376–385;
- 1dT. Tenson, A. S. Mankin, Peptides 2001, 22, 1661–1668;
- 1eS. Tripathi, P. S. Kloss, A. S. Mankin, J. Biol. Chem. 1998, 273, 20073–20077;
- 1fT. Tenson, L. Xiong, P. Kloss, A. S. Mankin, J. Biol. Chem. 1997, 272, 17425–17430;
- 1gM. Dam, S. Douthwaite, T. Tenson, A. S. Mankin, J. Mol. Biol. 1996, 259, 1–6;
- 1hT. Tenson, A. DeBlasio, A. S. Mankin, Proc. Natl. Acad. Sci. USA 1996, 93, 5641–5646.
- 2M. Lovmar, K. Nilsson, V. Vimberg, T. Tenson, M. Nervall, M. Ehrenberg, J. Biol. Chem. 2006, 281, 6742–6750.
- 3L. Verdier, J. Gharbi-Benarous, G. Bertho, P. Mauvais, J.-P. Girault, Biochemistry 2002, 41, 4218–4229.
- 4
- 4aK. H. Nierhaus in Protein Synthesis and Ribosome Structure (Eds.: ), Wiley-VCH, Weinheim, 2004, pp. 323–336;
10.1002/3527603433.ch8 Google Scholar
- 4bD. N. Wilson, K. H. Nierhaus, Angew. Chem. 2003, 115, 3586–3610;
10.1002/ange.200200544 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 3464–3486;
- 4cY. Lapidot, N. De Groot, S. Rappoport, Biochim. Biophys. Acta Nucleic Acids Protein Synth. 1969, 182, 105–112.
- 5M. A. Darken, Pharmacol. Rev. 1964, 16, 223–243.
- 6
- 6aM. Koch, Y. Huang, M. Sprinzl, Angew. Chem. 2008, 120, 7352–7355;
10.1002/ange.200801511 Google ScholarAngew. Chem. Int. Ed. 2008, 47, 7242–7245;
- 6bK. Lang, M. Erlacher, D. N. Wilson, R. Micura, N. Polacek, Chem. Biol. 2008, 15, 485–492;
- 6cK. S. Huang, N. Carrasco, E. Pfund, S. A. Strobel, Biochemistry 2008, 47, 8822–8827;
- 6dS. Chládek, Sprinzl, Angew. Chem. 1985, 97, 377–398; Angew. Chem. Int. Ed. Engl. 1985, 24, 371–391.
- 7S. R. Waldvogel, W. Pfleiderer, Helv. Chim. Acta 1998, 81, 46–58.
- 8Y. C. Jack Chen, F. Hansske, K. D. Janda, M. J. Robins, J. Org. Chem. 1991, 56, 3410–3413.
- 9
- 9aC. Höbartner, R. Rieder, C. Kreutz, B. Puffer, K. Lang, A. Polonskaia, A. Serganov, R. Micura, J. Am. Chem. Soc. 2005, 127, 12035–12045;
- 9bH. Moroder, C. Kreutz, K. Lang, A. Serganov, R. Micura, J. Am. Chem. Soc. 2006, 128, 9909–9918;
- 9cR. Micura, C. Höbartner, R. Rieder, C. Kreutz, B. Puffer, K. Lang, H. Moroder, Curr. Protoc. Nucl. Acid Chem. 2007, Wiley, C1.15.1.–C1.15.34.
- 10
- 10aH. Chapuis, P. Strazewski, Tetrahedron 2006, 62, 12108–12115;
- 10bA. Charafeddine, W. Dayoub, H. Chapuis, P. Strazewski, Chem. Eur. J. 2007, 13, 5566–5584;
- 10cB. Y. Michel, K. S. Krishnakumar, P. Strazewski, Synlett 2008, 2461–2464;
- 10dH. Saneyoshi, B. Y. Michel, Y. Choi, P. Strazewski, V. E. Marquez, J. Org. Chem. 2008, 73, 9435–9438.
- 11V. Marchán, C. Rodríguez-Tanty, M. Estrada, E. Pedroso, A. Grandas, Eur. J. Org. Chem. 2000, 2495–2500.
- 12
- 12aK. H. Nierhaus in Protein Synthesis and Ribosome Structure (Eds.: ), Wiley-VCH, Weinheim, 2004, pp. 207–217;
10.1002/3527603433.ch6 Google Scholar
- 12bD. Moazed, H. F. Noller, Cell 1989, 57, 585–597.
- 13
- 13aK. Okuda, A. C. Seila, S. A. Strobel, Tetrahedron 2004, 60, 12101–12112;
- 13bK. Okuda, A. C. Seila, S. A. Strobel, Biochemistry 2005, 44, 6675–6684;
- 13cT. M. Schmeing, A. C. Seila, J. L. Hansen, B. Freeborn, J. K. Soukup, S. A. Scaringe, S. A. Strobel, P. B. Moore, T. A. Steitz, Nat. Struct. Biol. 2002, 9, 225–230;
- 13dK. S. Huang, J. S. Weinger, E. B. Butler, S. A. Strobel, J. Am. Chem. Soc. 2006, 128, 3108–3109;
- 13eJ. S. Weinger, D. Kitchen, S. A. Scaringe, S. A. Strobel, G. W. Muth, Nucleic Acids Res. 2004, 32, 1502–1511;
- 13fA. V. Manuilov, S. S. Hixson, R. A. Zimmermann, RNA 2007, 13, 793–800;
- 13gT. M. Schmeing, K. S. Huang, D. E. Kitchen, S. A. Strobel, T. A. Steitz, Mol. Cell 2005, 20, 437–448;
- 13hP. Nissen, J. Hansen, N. Ban, P. B. Moore, T. A. Steitz, Science 2000, 289, 920–930;
- 13iM. Zhong, S. A. Strobel, Org. Lett. 2006, 8, 55–58;
- 13jM. Zhong, S. A. Strobel, J. Org. Chem. 2008, 73, 603–611.
- 14
- 14aS. Terenzi, E. Biała, N. Q. Nguyen-Trung, P. Strazewski, Angew. Chem. 2003, 115, 3015–3018;
10.1002/ange.200350926 Google ScholarAngew. Chem. Int. Ed. 2003, 42, 2909–2912;
- 14bA. N. Lazar, A. W. Coleman, S. Terenzi, P. Strazewski, Chem. Commun. 2006, 63–65;
- 14cN. Q. Nguyen-Trung, S. Terenzi, G. Scherer, P. Strazewski, Org. Lett. 2003, 5, 2603–2606;
- 14dN. Q. Nguyen-Trung, O. Botta, S. Terenzi, P. Strazewski, J. Org. Chem. 2003, 68, 2038–2041;
- 14eB. Zhang, L. Zhang, L. Sun, Z. Cui, Org. Lett. 2002, 4, 3615–3618.
- 15
- 15aM. Chemama, M. Fonvielle, M. Arthur, J. M. Valéry, M. Etheve-Quelquejeu, Chem. Eur. J. 2009, 15, 1929–1938;
- 15bM. Chemama, M. Fonvielle, R. Villet, M. Arthur, J. M. Valéry, M. Etheve-Quelquejeu, J. Am. Chem. Soc. 2007, 129, 12642–12643.
- 16K. Lang, R. Micura, Nat. Protoc. 2008, 3, 1457–1466.
- 17N. Vazquez-Laslop, C. Thum, A. S. Mankin, Mol. Cell 2008, 30, 190–202.
