Template Assembled Synthetic Proteins (TASP) as Functional Mimetics of Proteins
1996; Wiley; Volume: 35; Issue: 13-14 Linguagem: Inglês
10.1002/anie.199614821
ISSN1521-3773
AutoresManfred Mutter, Pascal Dumy, Patrick Garrouste, Christian W. Lehmann, Marc Mathieu, Cristina Peggion, Stéphane Peluso, Alain Razaname, Gabriele Tuchscherer,
Tópico(s)Click Chemistry and Applications
ResumoAngewandte Chemie International Edition in EnglishVolume 35, Issue 13-14 p. 1482-1485 Communication Template Assembled Synthetic Proteins (TASP) as Functional Mimetics of Proteins† Prof. Dr. Manfred Mutter, Corresponding Author Prof. Dr. Manfred Mutter Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Pascal Dumy, Dr. Pascal Dumy Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Patrick Garrouste, Dr. Patrick Garrouste Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Christian Lehmann, Dr. Christian Lehmann Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Marc Mathieu, Dipl.-Chem. Marc Mathieu Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Cristina Peggion, Dipl.-Chem. Cristina Peggion Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Stéphane Peluso, Dipl.-Chem. Stéphane Peluso Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Alain Razaname, Dr. Alain Razaname Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Gabriele Tuchscherer, Dr. Gabriele Tuchscherer Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this author Prof. Dr. Manfred Mutter, Corresponding Author Prof. Dr. Manfred Mutter Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Pascal Dumy, Dr. Pascal Dumy Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Patrick Garrouste, Dr. Patrick Garrouste Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Christian Lehmann, Dr. Christian Lehmann Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Marc Mathieu, Dipl.-Chem. Marc Mathieu Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Cristina Peggion, Dipl.-Chem. Cristina Peggion Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDipl.-Chem. Stéphane Peluso, Dipl.-Chem. Stéphane Peluso Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Alain Razaname, Dr. Alain Razaname Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this authorDr. Gabriele Tuchscherer, Dr. Gabriele Tuchscherer Institute for Organic Chemistry, University of Lausanne BCH-Dorigny, CH-1015 Lausanne (Switzerland) Fax: Int. code +(21)692-4015 e-mail: [email protected]Search for more papers by this author First published: July 1996 https://doi.org/10.1002/anie.199614821Citations: 82 † This work was supported by the Swiss National Science Foundation. AboutPDF 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 The bare essentials of a functional protein are all that are retained when the structural domain of a native protein is replaced by a synthetic template molecule (see picture below). New strategies for the synthesis of this novel type of template-assembled synthetic peptide (TASP) provide functional mimetics of receptors and antibodies. References 1 G. Tuchscherer, M. Mutter, J. Biotechnol. 1995, 41, 197. 2 G. Tuchscherer, B. Dörner, U. Sila, B. Kamber, M. Mutter, Tetrahedron 1993, 49, 3559. 3 J. W. Bryson, S. F. Betz, H. S. Lu, D. J. Suich, H. X. Zhou, K. T. O'Neil, W. F. DeGrado, Science 1995, 270, 935. 4 J. P. Schneider, J. W. Kelly, Chem. Rev. 1995, 95, 2169. 5 M. Mutter, S. Vuilleumier, Angew. Chem. 1989, 101, 551; Angew. Chem. Int. Ed. Engl. 1989, 28, 535. 6 M. Mutter, G. Tuchscherer, C. Miller, K. H. Altmann, R. I. Carey, D. F. Wyss, A. M. Labhardt, J. E. Rivier, J. Am. Chem. Soc. 1992, 114, 1463. 7 G. Tuchscherer, M. Mutter, J. Peptide Sci. 1995, 1, 3. 8 G. Tuchscherer, C. Servis, G. Corradin, U. Blum, J. Rivier, M. Mutter, Protein Sci. 1992, 1, 1377. 9 K. Rose, J. Am. Chem. Soc. 1994, 116, 30. 10 P. E. Dawson, S. B. H. Kent, J. Am. Chem. Soc. 1993, 115, 7263. 11 G. Tuchscherer, Tetrahedron Lett. 1993, 34, 8419. 12 A. Nefzi, X. Sun, M. Mutter, Tetrahedron Lett. 1994, 36, 229. 13 I. Ernest, J. Kalvoda, C. Sigel, G. Rihs, H. Fritz, M. J. J. Blommers, F. Raschdorf, E. Francotte, M. Mutter, Helv. Chim. Acta 1993, 76, 1539. 14 P. Dumy, I. M. Eggleston, S. E. Cervigni, U. Sila, X. Sun, M. Mutter, Tetrahedron Lett. 1995, 36, 1255. 15 P. Dumy, I. M. Eggleston, G. Esposito, S. Nicula, M. Mutter, Biopolymers 1996, in press. 16 R. A. Houghten, C. Pinilla, S. E. Blondelle, J. R. Appel, C. T. Dooley, J. H. Cuervo, Nature 1991, 354, 84. 17 According to cyclization theory, the cyclization equilibrium constant K is proportional to the volume density W(r) of the head to tail vectors 〈r〉 (where 〈〉 denotes the statistical mechanical average of r over all accessible loop conformations). Assuming in a first approximation a random coil conformation of the flexible loop sequence and a Gaussian distribution of 〈r〉, W(r) at a fixed distance r1 of the reacting chain ends (r1 corresponds to the distance between the loop attachment sites on the template) approaches a maximal value for r1 ≈ 〈r〉. Consequently, the tendency for ring closure in loop condensation reactions (where r1 → 〈r〉) is predicted to be higher than in regular cyclization reactions (where r1 → 0). see: M. Mutter, J. Am. Chem. Soc. 1977, 99, 8307. 18 Y. Satow, G. H. Cohen, E. A. Padlan, D. R. Davies, J. Mol. Biol. 1986, 593, 190. 19 G. B. Bloomberg, D. Askin, A. R. Gargaro, M. J. A. Tanner, Tetrahedron Lett. 1993, 34, 4709. 20 R. W. Woody, Peptides, (NY) 1985, 7, 15. 21 These studies will be subject of a separate publication. 22 J. M. Stewart, J. D. Young, Solid Phase Peptide Synthesis, 2nd ed., Pierce Chemical, Rockford, IL, 1984. 23 P. R. Gerber, Biopolymers 1992, 32, 1003. 24 P. R. Gerber, K. Müller, J. Comput. Aided Mol. Design 1995, 9, 251. 25 P. J. Flory, Statistical Mechanics of Chain Molecules, Interscience, New York, NY, 1969. 26 G. Fransson, B. K. S. Lundberg, Acta Chem. Scand 1972, 26, 3969. Citing Literature Volume35, Issue13-14July 1996Pages 1482-1485 ReferencesRelatedInformation
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