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Asymmetric Enzymatic Hydration of Hydroxystyrene Derivatives

2013; Wiley; Volume: 52; Issue: 8 Linguagem: Inglês

10.1002/anie.201207916

ISSN

1521-3773

Autores

Christiane Wuensch, Johannes Gross, Georg Steinkellner, Karl Gruber, Silvia M. Glueck, Kurt Faber,

Tópico(s)

Biochemical and biochemical processes

Resumo

Angewandte Chemie International EditionVolume 52, Issue 8 p. 2293-2297 Communication Asymmetric Enzymatic Hydration of Hydroxystyrene Derivatives† Christiane Wuensch, Christiane Wuensch ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)Search for more papers by this authorJohannes Gross, Johannes Gross ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)Search for more papers by this authorDr. Georg Steinkellner, Dr. Georg Steinkellner ACIB GmbH c/o Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)Search for more papers by this authorProf. Karl Gruber, Prof. Karl Gruber Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)Search for more papers by this authorDr. Silvia M. Glueck, Corresponding Author Dr. Silvia M. Glueck [email protected] ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria) Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)=== Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===Search for more papers by this authorProf. Kurt Faber, Corresponding Author Prof. Kurt Faber [email protected] Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria) Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)=== Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===Search for more papers by this author Christiane Wuensch, Christiane Wuensch ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)Search for more papers by this authorJohannes Gross, Johannes Gross ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)Search for more papers by this authorDr. Georg Steinkellner, Dr. Georg Steinkellner ACIB GmbH c/o Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)Search for more papers by this authorProf. Karl Gruber, Prof. Karl Gruber Institute of Molecular Biosciences, University of Graz, Humboldtstrasse 50, 8010 Graz (Austria)Search for more papers by this authorDr. Silvia M. Glueck, Corresponding Author Dr. Silvia M. Glueck [email protected] ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria) Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)=== Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===Search for more papers by this authorProf. Kurt Faber, Corresponding Author Prof. Kurt Faber [email protected] Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria) Silvia M. Glueck, ACIB GmbH c/o Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)=== Kurt Faber, Department of Chemistry, Organic & Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz (Austria)===Search for more papers by this author First published: 17 January 2013 https://doi.org/10.1002/anie.201207916Citations: 67 † This work has been supported by the Austrian BMWFJ, BMVIT, SFG, Standortagentur Tirol, and ZIT through the Austrian FFG-COMET- Funding Program. Byung-Gee Kim (School of Chemical and Biological Engineering, Seoul National University, Seoul, South Korea) is cordially thanked for the generous donation of phenolic acid decarboxylase plasmids. 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 Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract More than one activity: Owing to their hydratase activity, phenolic acid decarboxylases catalyze the regio- and stereoselective addition of H2O across the CC double bond of hydroxystyrene derivatives yielding (S)-4-(1-hydroxyethyl)phenols with up to 82 % conversion and 71 % ee. Based on structure analysis and molecular docking simulations, a catalytic mechanism for this novel enzymatic reaction is proposed. 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