Oxidative Deselenization of Selenocysteine: Applications for Programmed Ligation at Serine
Dr. Lara R. Malins
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
These authors contributed equally to this work.
Search for more papers by this authorDr. Nicholas J. Mitchell
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
These authors contributed equally to this work.
Search for more papers by this authorDr. Sheena McGowan
Department of Biochemistry and Molecular Biology, Monash University, Melbourne, VIC 3800 (Australia)
Search for more papers by this authorCorresponding Author
Prof. Richard J. Payne
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.htmlSearch for more papers by this authorDr. Lara R. Malins
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
These authors contributed equally to this work.
Search for more papers by this authorDr. Nicholas J. Mitchell
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
These authors contributed equally to this work.
Search for more papers by this authorDr. Sheena McGowan
Department of Biochemistry and Molecular Biology, Monash University, Melbourne, VIC 3800 (Australia)
Search for more papers by this authorCorresponding Author
Prof. Richard J. Payne
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.html
School of Chemistry, The University of Sydney, NSW 2006 (Australia) http://sydney.edu.au/science/chemistry/∼payne/index.htmlSearch for more papers by this authorAbstract
Despite the unique chemical properties of selenocysteine (Sec), ligation at Sec is an under-utilized methodology for protein synthesis. We describe herein an unprecedented protocol for the conversion of Sec to serine (Ser) in a single, high-yielding step. When coupled with ligation at Sec, this transformation provides a new approach to programmed ligations at Ser residues. This new reaction is compatible with a wide range of functionality, including the presence of unprotected amino acid side chains and appended glycans. The utility of the methodology is demonstrated in the rapid synthesis of complex glycopeptide fragments of the epithelial glycoproteins MUC5AC and MUC4 and through the total synthesis of the structured, cysteine (Cys)-free protein eglin C.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
| Filename | Description |
|---|---|
| ange_201504639_sm_miscellaneous_information.pdf23.5 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776–779.
- 2S. B. Kent, Chem. Soc. Rev. 2009, 38, 338–351.
- 3
- 3aD. P. Gamblin, E. M. Scanlan, B. G. Davis, Chem. Rev. 2009, 109, 131–163;
- 3bR. J. Payne, C. H. Wong, Chem. Commun. 2010, 46, 21–43;
- 3cL. Raibaut, N. Ollivier, O. Melnyk, Chem. Soc. Rev. 2012, 41, 7001–7015.
- 4
- 4aH. Rohde, O. Seitz, Biopolymers 2010, 94, 551–559;
- 4bP. E. Dawson, Isr. J. Chem. 2011, 51, 862–867;
- 4cC. P. R. Hackenberger, D. Schwarzer, Angew. Chem. Int. Ed. 2008, 47, 10030–10074; Angew. Chem. 2008, 120, 10182–10228;
- 4dL. R. Malins, R. J. Payne, Curr. Opin. Chem. Biol. 2014, 22, 70–78.
- 5
- 5aL. Z. Yan, P. E. Dawson, J. Am. Chem. Soc. 2001, 123, 526–533;
- 5bQ. Wan, S. J. Danishefsky, Angew. Chem. Int. Ed. 2007, 46, 9248–9252; Angew. Chem. 2007, 119, 9408–9412.
- 6
- 6aD. Crich, A. Banerjee, J. Am. Chem. Soc. 2007, 129, 10064–10065;
- 6bJ. Chen, Q. Wan, Y. Yuan, J. L. Zhu, S. J. Danishefsky, Angew. Chem. Int. Ed. 2008, 47, 8521–8524; Angew. Chem. 2008, 120, 8649–8652;
- 6cC. Haase, H. Rohde, O. Seitz, Angew. Chem. Int. Ed. 2008, 47, 6807–6810; Angew. Chem. 2008, 120, 6912–6915;
- 6dZ. Harpaz, P. Siman, K. S. A. Kumar, A. Brik, ChemBioChem 2010, 11, 1232–1235;
- 6eR. L. Yang, K. K. Pasunooti, F. P. Li, X. W. Liu, C. F. Liu, J. Am. Chem. Soc. 2009, 131, 13592–13593;
- 6fK. S. Ajish Kumar, M. Haj-Yahya, D. Olschewski, H. A. Lashuel, A. Brik, Angew. Chem. Int. Ed. 2009, 48, 8090–8094; Angew. Chem. 2009, 121, 8234–8238;
- 6gJ. Chen, P. Wang, J. L. Zhu, Q. Wan, S. J. Danishefsky, Tetrahedron 2010, 66, 2277–2283;
- 6hL. R. Malins, K. M. Cergol, R. J. Payne, ChemBioChem 2013, 14, 559–563;
- 6iR. E. Thompson, B. Chan, L. Radom, K. A. Jolliffe, R. J. Payne, Angew. Chem. Int. Ed. 2013, 52, 9723–9727; Angew. Chem. 2013, 125, 9905–9909;
- 6jL. R. Malins, K. M. Cergol, R. J. Payne, Chem. Sci. 2014, 5, 260–266;
- 6kS. Y. Shang, Z. P. Tan, S. W. Dong, S. J. Danishefsky, J. Am. Chem. Soc. 2011, 133, 10784–10786;
- 6lK. M. Cergol, R. E. Thompson, L. R. Malins, P. Turner, R. J. Payne, Org. Lett. 2014, 16, 290–293;
- 6mP. Siman, S. V. Karthikeyan, A. Brik, Org. Lett. 2012, 14, 1520–1523;
- 6nZ. P. Tan, S. Y. Shang, S. J. Danishefsky, Angew. Chem. Int. Ed. 2010, 49, 9500–9503; Angew. Chem. 2010, 122, 9690–9693;
- 6oL. R. Malins, R. J. Payne, Aust. J. Chem. 2015, 68, 521–537;
- 6pL. R. Malins, A. M. Giltrap, L. J. Dowman, R. J. Payne, Org. Lett. 2015, 17, 2070–2073;
- 6qK. Sato, K. Kitakaze, T. Nakamura, N. Naruse, K. Aihara, A. Shigenaga, T. Inokuma, D. Tsuji, K. Itoh, A. Otaka, Chem. Commun. 2015, 51, 9946–9948.
- 7To the best of our knowledge, selective desulfurization reactions have only been reported for ligation–desulfurization at β-thiol Asp residues (see reference [6i]).
- 8
- 8aR. Quaderer, A. Sewing, D. Hilvert, Helv. Chim. Acta 2001, 84, 1197–1206;
- 8bR. J. Hondal, B. L. Nilsson, R. T. Raines, J. Am. Chem. Soc. 2001, 123, 5140–5141;
- 8cM. D. Gieselman, L. Xie, W. A. van der Donk, Org. Lett. 2001, 3, 1331–1334.
- 9N. Metanis, E. Keinan, P. E. Dawson, Angew. Chem. Int. Ed. 2010, 49, 7049–7053; Angew. Chem. 2010, 122, 7203–7207.
- 10
- 10aS. D. Townsend, Z. Tan, S. Dong, S. Shang, J. A. Brailsford, S. J. Danishefsky, J. Am. Chem. Soc. 2012, 134, 3912–3916;
- 10bL. R. Malins, R. J. Payne, Org. Lett. 2012, 14, 3142–3145;
- 10cL. R. Malins, N. J. Mitchell, R. J. Payne, J. Pept. Sci. 2014, 20, 64–77.
- 11Dawson and co-workers also observed a small amount of Sec to Ser conversion in their unoptimized deselenization conditions (see reference [9]).
- 12
- 12aM. Y. Lutsky, N. Nepomniaschiy, A. Brik, Chem. Commun. 2008, 1229–1231;
- 12bH. Hojo, C. Ozawa, H. Katayama, A. Ueki, Y. Nakahara, Y. Nakahara, Angew. Chem. Int. Ed. 2010, 49, 5318–5321; Angew. Chem. 2010, 122, 5446–5449.
- 13M. El Khatib, M. Elagawany, F. Jabeen, E. Todadze, O. Bol’shakov, A. Oliferenko, L. Khelashvili, S. A. el-Feky, A. Asiri, A. R. Katritzky, Org. Biomol. Chem. 2012, 10, 4836–4838.
- 14
- 14aY. Zhang, C. Xu, H. Y. Lam, C. L. Lee, X. Li, Proc. Natl. Acad. Sci. USA 2013, 110, 6657–6662;
- 14bX. Li, H. Y. Lam, Y. Zhang, C. K. Chan, Org. Lett. 2010, 12, 1724–1727.
- 15R. Okamoto, Y. Kajihara, Angew. Chem. Int. Ed. 2008, 47, 5402–5406; Angew. Chem. 2008, 120, 5482–5486.
- 16I. Pusterla, J. W. Bode, Nature Chem. 2015, 7, 668–672.
- 17R. J. Kennedy, A. M. Stock, J. Org. Chem. 1960, 25, 1901–1906.
- 18
- 18aL. Ju, A. R. Lippert, J. W. Bode, J. Am. Chem. Soc. 2008, 130, 4253–4255;
- 18bJ. W. Bode, R. M. Fox, K. D. Baucom, Angew. Chem. Int. Ed. 2006, 45, 1248–1252; Angew. Chem. 2006, 118, 1270–1274;
- 18cA. O. Ogunkoya, V. R. Pattabiraman, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 9693–9697; Angew. Chem. 2012, 124, 9831–9835;
- 18dV. R. Pattabiraman, A. O. Ogunkoya, J. W. Bode, Angew. Chem. Int. Ed. 2012, 51, 5114–5118; Angew. Chem. 2012, 124, 5204–5208.
- 19C. P. Hackenberger, Org. Biomol. Chem. 2006, 4, 2291–2295.
- 20
- 20aD. M. McDonald, B. L. Wilkinson, L. Corcilius, M. Thaysen-Andersen, S. N. Byrne, R. J. Payne, Chem. Commun. 2014, 50, 10273–10276;
- 20bB. L. Wilkinson, S. Day, R. Chapman, S. Perrier, V. Apostolopoulos, R. J. Payne, Chem. Eur. J. 2012, 18, 16540–16548;
- 20cB. L. Wilkinson, S. Day, L. R. Malins, V. Apostolopoulos, R. J. Payne, Angew. Chem. Int. Ed. 2011, 50, 1635–1639; Angew. Chem. 2011, 123, 1673–1677.
- 21
- 21aU. Seemüller, M. Meier, K. Ohlsson, H. P. Muller, H. Fritz, Hoppe-Seyler′s Z. Physiol. Chem. 1977, 358, 1105–1107;
- 21bU. Seemüller, M. Eulitz, H. Fritz, A. Strobl, Hoppe-Seyler′s Z. Physiol. Chem. 1980, 361, 1841–1846.
- 22H. Rink, M. Liersch, P. Sieber, F. Meyer, Nucleic Acids Res. 1984, 12, 6369–6387.
- 23W. Y. Lu, M. A. Starovasnik, J. J. Dwyer, A. A. Kossiakoff, S. B. Kent, W. Lu, Biochemistry 2000, 39, 3575–3584.
- 24N. Ollivier, A. Blanpain, E. Boll, L. Raibaut, H. Drobecq, O. Melnyk, Org. Lett. 2014, 16, 4032–4035.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.
