Title: Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity
Abstract: Angewandte Chemie International EditionVolume 47, Issue 45 p. 8657-8660 Communication Highly Stereospecific Generation of Helical Chirality by Imprinting with Amino Acids: A Universal Sensor for Amino Acid Enantiopurity† Hyunwoo Kim, Hyunwoo Kim Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorSoon Mog So Dr., Soon Mog So Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorCindy Pai-Hui Yen, Cindy Pai-Hui Yen Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorElisângela Vinhato Dr., Elisângela Vinhato Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorAlan J. Lough Dr., Alan J. Lough Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorJong-In Hong Prof. Dr., Jong-In Hong Prof. Dr. [email protected] Department of Chemistry, Seoul National University, Seoul 151-747 (Korea)Search for more papers by this authorHae-Jo Kim Prof. Dr., Hae-Jo Kim Prof. Dr. [email protected] Department of Chemistry, Kyonggi University, Suwon 443-760 (Korea)Search for more papers by this authorJik Chin Prof. Dr., Jik Chin Prof. Dr. [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this author Hyunwoo Kim, Hyunwoo Kim Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorSoon Mog So Dr., Soon Mog So Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorCindy Pai-Hui Yen, Cindy Pai-Hui Yen Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorElisângela Vinhato Dr., Elisângela Vinhato Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorAlan J. Lough Dr., Alan J. Lough Dr. Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this authorJong-In Hong Prof. Dr., Jong-In Hong Prof. Dr. [email protected] Department of Chemistry, Seoul National University, Seoul 151-747 (Korea)Search for more papers by this authorHae-Jo Kim Prof. Dr., Hae-Jo Kim Prof. Dr. [email protected] Department of Chemistry, Kyonggi University, Suwon 443-760 (Korea)Search for more papers by this authorJik Chin Prof. Dr., Jik Chin Prof. Dr. [email protected] Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6 (Canada), Fax: (+1) 416-978-7113Search for more papers by this author First published: 21 October 2008 https://doi.org/10.1002/anie.200803116Citations: 90 † We thank the Natural Sciences and Engineering Research Council of Canada, Korea Research Foundation (Grant No. 2007-314-C00172), and Seoul R&BD for financial support. E.V. thanks CNPq of Brazil for a postdoctoral fellowship. 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 Helical chirality can be imprinted onto a 2,2′-dihydroxybenzophenone derivative (see picture) in a highly stereospecific manner. A single amino acid combines with the receptor to form an imine with two internal hydrogen bonds. The azo group allows sensing of amino acid enantiopurity by circular dichroism spectroscopy. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200803116_sm_miscellaneous_information.pdf3.5 MB miscellaneous information 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. References 1S. Superchi, R. Bisaccia, D. Casarini, A. Laurita, C. Rosini, J. Am. Chem. Soc. 2006, 128, 6893–6902. 2 2aS. Superchi, D. Casarini, A. Laurita, A. Bavoso, C. Rosini, Angew. Chem. 2001, 113, 465–468; Angew. Chem. Int. Ed. 2001, 40, 451–454; 2bJ. Gawroński, M. Kwit, K. Gawrońska, Org. Lett. 2002, 4, 4185–4188; 2cS. Hosoi, M. Kamiya, T. Ohta, Org. Lett. 2001, 3, 3659–3662; 2dR. Eelkema, B. L. Feringa, J. Am. 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