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Kinetically Controlled Ligation for the Convergent Chemical Synthesis of Proteins

2006; Wiley; Volume: 45; Issue: 24 Linguagem: Inglês

10.1002/anie.200600702

ISSN

1521-3773

Autores

Duhee Bang, Brad L. Pentelute, Stephen B. H. Kent,

Tópico(s)

Microbial Natural Products and Biosynthesis

Resumo

Angewandte Chemie International EditionVolume 45, Issue 24 p. 3985-3988 Communication Kinetically Controlled Ligation for the Convergent Chemical Synthesis of Proteins† Duhee Bang Dr., Duhee Bang Dr. Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this authorBrad L. Pentelute, Brad L. Pentelute Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this authorStephen B. H. Kent Prof., Stephen B. H. Kent Prof. [email protected] Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this author Duhee Bang Dr., Duhee Bang Dr. Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this authorBrad L. Pentelute, Brad L. Pentelute Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this authorStephen B. H. Kent Prof., Stephen B. H. Kent Prof. [email protected] Department of Chemistry, Institute for Biophysical Dynamics, Center for Integrative Science, The University of Chicago, 929 East 57th Street, Chicago, IL 60637, USA, Fax: (+1) 773-702-0439Search for more papers by this author First published: 01 June 2006 https://doi.org/10.1002/anie.200600702Citations: 254 † This work was supported by funding from the DOE GTL program (grant DE-FG02-04ER63786 to S.B.K). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Graphical Abstract Converging on the goal: New chemistry enables the key Cys-peptide-(αthioester) intermediate to be extended by ligation at either the N or C termini in a controlled fashion. This approach forms the basis for a set of novel tactics for the fully convergent synthesis of proteins by the chemical ligation of multiple peptide segments. References 1P. E. Dawson, S. B. Kent, Annu. Rev. Biochem. 2000, 69, 923– 960. 2G. G. Kochendoerfer, S. Y. Chen, F. Mao, S. Cressman, S. Traviglia, H. Shao, C. L. Hunter, D. W. Low, E. N. Cagle, M. Carnevali, V. Gueriguian, P. J. Keogh, H. Porter, S. M. Stratton, M. C. Wiedeke, J. Wilken, J. Tang, J. J. Levy, L. P. Miranda, M. M. Crnogorac, S. Kalbag, P. Botti, J. Schindler-Horvat, L. Savatski, J. W. Adamson, A. Kung, S. B. Kent, J. A. Bradburne, Science 2003, 299, 884– 887. 3D. Bang, S. B. Kent, Angew. Chem. 2004, 116, 2588– 2592; Angew. Chem. Int. Ed. 2004, 43, 2534– 2538. 4D. Bang, G. I. Makhatadze, V. Tereshko, A. A. Kossiakoff, S. B. Kent, Angew. Chem. 2005, 117, 3920– 3924; Angew. Chem. Int. Ed. 2005, 44, 3852– 3856. 5Z. Wu, J. Alexandratos, B. Ericksen, J. Lubkowski, R. C. Gallo, W. Lu, Proc. Natl. Acad. Sci. USA 2004, 101, 11587– 11592. 6M. Schnölzer, S. B. Kent, Science 1992, 256, 221– 225. 7J. B. Hendrickson, J. Am. Chem. Soc. 1977, 99, 5439– 5450. 8P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science 1994, 266, 776– 779. 9D. Bang, S. B. Kent, Proc. Natl. Acad. Sci. USA 2005, 102, 5014– 5019. 10L. E. Canne, P. Botti, R. J. Simon, Y. Chen, E. A. Dennis, S. B. Kent, J. Am. Chem. Soc. 1999, 121, 8720– 8727. 11G. Casi, D. Hilvert, Curr. Opin. Struct. Biol. 2003, 13, 589– 594. 12Under native chemical ligation reaction conditions, the Cys-peptide 2-(αthioester) will itself undergo multiple reactions to form cyclic (Cys-peptide 2), Cys-peptide 2-Cys-peptide 2-(αthioester), and other oligomerization and cyclization products. See: 12aL. Zhang, J. P. Tam, J. Am. Chem. Soc. 1997, 119, 2363– 2370; 12bT. C. Evans, J. Benner, M.-Q. Xu, J. Biol. Chem. 1999, 274, 18359– 18363. 13T. M. Hackeng, J. H. Griffin, P. E. Dawson, Proc. Natl. Acad. Sci. USA 1999, 96, 10068– 10073. 14P. E. Dawson, M. J. Churchill, M. R. Ghadiri, S. B. H. Kent, J. Am. Chem. Soc. 1997, 119, 4325– 4329. 15M. M. Teeter, J. A. Mazer, J. J. L'Italien, Biochemistry 1981, 20, 5437– 5443. 16C. Jelsch, M. M. Teeter, V. Lamzin, V. Pichon-Pesme, R. H. Blessing, C. Lecomte, Proc. Natl. Acad. Sci. USA 2000, 97, 3171– 3176. 17D. Bang, N. Chopra, S. B. Kent, J. Am. Chem. Soc. 2004, 126, 1377– 1383. 18H. J. Musiol, S. Dong, M. Kaiser, R. Bausinger, A. Zumbusch, U. Bertsch, L. Moroder, ChemBioChem 2005, 6, 625– 628. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z600702_s.pdf or from the author. 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. Volume45, Issue24June 12, 2006Pages 3985-3988 ReferencesRelatedInformation

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