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Analysis of the Topology of the Chromophore Binding Pocket of Phytochromes by Variation of the Chromophore Substitution Pattern

2001; Wiley; Volume: 40; Issue: 6 Linguagem: Inglês

10.1002/1521-3773(20010316)40

1521-3773

Uwe Robben, Ingo Lindner, Wolfgang Gärtner, Kurt Schaffner,

Plant and animal studies

Angewandte Chemie International EditionVolume 40, Issue 6 p. 1048-1050 Communication Analysis of the Topology of the Chromophore Binding Pocket of Phytochromes by Variation of the Chromophore Substitution Pattern Uwe Robben Dr., Uwe Robben Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorIngo Lindner Dr., Ingo Lindner Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorWolfgang Gärtner Prof. Dr., Wolfgang Gärtner Prof. Dr. [email protected] Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorKurt Schaffner Prof. Dr., Kurt Schaffner Prof. Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this author Uwe Robben Dr., Uwe Robben Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorIngo Lindner Dr., Ingo Lindner Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorWolfgang Gärtner Prof. Dr., Wolfgang Gärtner Prof. Dr. [email protected] Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this authorKurt Schaffner Prof. Dr., Kurt Schaffner Prof. Dr. Max-Planck-Institut für Strahlenchemie Postfach 101365, 45413 Mülheim an der Ruhr (Germany) Fax: (+49) 208-306-3951Search for more papers by this author First published: 14 March 2001 https://doi.org/10.1002/1521-3773(20010316)40:6 3.0.CO;2-9Citations: 13Read 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The assembly kinetics of open-chain tetrapyrroles in a recombinant apophytochrome and the thermal reversal of the Pfr to the Pr form of the phytochrome are strongly affected by steric interactions between the protein and the chromophore. Relative to the chromoprotein with a naturally occurring chromophore (1), bulkier alkyl groups on ring D regioselectively retard the incorporation and covalent binding (whereby C17 derivatives, particularly the 17-CH(CH3)2 derivative 2, have a larger effect than C18 derivatives), and either decrease or increase the thermal stability of the Pfr form with increasing substituent size at C17/C18, respectively (the 18-C(CH3)3 derivative 3 shows the largest effect here). References 1 I. Lindner, B. Knipp, S. E. Braslavsky, W. Gärtner, K. Schaffner, Angew. Chem. 1998, 110, 1943–1946; Angew. Chem. Int. Ed. 1998, 37, 1843–1846. 2 For leading references on phytochromes, see: Photomorphogenesis in Plants ( ), 2nd ed., Kluwer, Dordrecht, 1994; S. E. Braslavsky, W. Gärtner, K. Schaffner, Plant Cell Environ. 1997, 20, 700–706. 3 3a The recombinant N-terminal half of phyA from oat (amino acids 1–595) shows all the photochemical and spectroscopic properties of the holoprotein. See, for example: D. Mozley, A. Remberg, W. Gärtner, Photochem. Photobiol. 1997, 66, 710–715. 3b Pr and Pfr stand for the thermally stable forms in the photocycle of the phytochromes (r=red, fr=far red). 4 For the thermally initiated Pfr→Pr isomerization, see: A. Remberg, A. Ruddat, S. E. Braslavsky, W. Gärtner, K. Schaffner, Biochemistry 1998, 37, 9983–9990. 5 The conformation of the free chromophore 5 b in homogeneous solution (methanol/0.5 % triethylamine) is not significantly affected by steric crowding due to the C17 isopropyl group, as judged by the absorption maxima of 360, 587, and 631 nm, which are comparable to those of 2, 3 a–c, and 5 b. 6 L. Li, J. T. Murphy, J. C. Lagarias, Biochemistry 1995, 34, 7923–7930. 7 See ref. [1] and references therein. A full publication of the synthesis of the new tetrapyrroles 2, 3 b, c, and 5 a, b is in preparation; see also: I. Lindner and U. Robben, PhD theses, Max-Planck-Institut für Strahlenchemie, Mülheim an der Ruhr, Gerhard-Mercator-Universität, Duisburg, 2000. 8 K. Kohori, M. Hashimoto, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 1994, 67, 3088–3093; M. A. Drinan, T. D. Lash, J. Heterocycl. Chem. 1994, 31, 255–257. 9 J. A. de Groot, R. van den Steen, R. Fokkens, J. Lugtenburg, Recl. Trav. Chim. Pays-Bas 1982, 101, 35–40. Citing Literature Volume40, Issue6March 16, 2001Pages 1048-1050 ReferencesRelatedInformation