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reading 2 - Tryptophan 7-Halogenase (PrnA) Structure...

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DOI: 10.1126/science.1116510 , 2216 (2005); 309 Science et al. Changjiang Dong, Chlorination Suggests a Mechanism for Regioselective Tryptophan 7-Halogenase (PrnA) Structure www.sciencemag.org (this information is current as of April 2, 2009 ): The following resources related to this article are available online at http://www.sciencemag.org/cgi/content/full/309/5744/2216 version of this article at: including high-resolution figures, can be found in the online Updated information and services, http://www.sciencemag.org/cgi/content/full/309/5744/2216/DC1 can be found at: Supporting Online Material http://www.sciencemag.org/cgi/content/full/309/5744/2216#otherarticles , 8 of which can be accessed for free: cites 30 articles This article 61 article(s) on the ISI Web of Science. cited by This article has been http://www.sciencemag.org/cgi/content/full/309/5744/2216#otherarticles 3 articles hosted by HighWire Press; see: cited by This article has been http://www.sciencemag.org/cgi/collection/biochem Biochemistry : subject collections This article appears in the following http://www.sciencemag.org/about/permissions.dtl in whole or in part can be found at: this article permission to reproduce of this article or about obtaining reprints Information about obtaining registered trademark of AAAS. is a Science 2005 by the American Association for the Advancement of Science; all rights reserved. The title Copyright American Association for the Advancement of Science, 1200 New York Avenue NW, Washington, DC 20005. (print ISSN 0036-8075; online ISSN 1095-9203) is published weekly, except the last week in December, by the Science on April 2, 2009 www.sciencemag.org Downloaded from
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Tryptophan 7-Halogenase (PrnA) Structure Suggests a Mechanism for Regioselective Chlorination Changjiang Dong, 1 Silvana Flecks, 2 Susanne Unversucht, 2 Caroline Haupt, 2 Karl-Heinz van Pe´e, 2 James H. Naismith 1 * Chlorinated natural products include vancomycin and cryptophycin A. Their biosynthesis involves regioselective chlorination by flavin-dependent halo- genases. We report the structural characterization of tryptophan 7- halogenase (PrnA), which regioselectively chlorinates tryptophan. Tryptophan and flavin adenine dinucleotide (FAD) are separated by a 10 angstrom–long tunnel and bound by distinct enzyme modules. The FAD module is conserved in halogenases and is related to flavin-dependent monooxygenases. On the basis of biochemical studies, crystal structures, and by analogy with monooxy- genases, we predict that FADH 2 reacts with O 2 to make peroxyflavin, which is decomposed by Cl . The resulting HOCl is guided through the tunnel to tryptophan, where it is activated to participate in electrophilic aromatic substitution. In addition to man-made chemicals, there are
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reading 2 - Tryptophan 7-Halogenase (PrnA) Structure...

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