Electrochemical Method for the Determination of Enantiomeric Excess of Binol Using Redox-Active Boronic Acids as Chiral Sensors
A chiral ferrocene-based boronic acid interacts with (R)- and (S)-Binol to form two complexes that exhibit significantly different ferrocene-based electrode potentials. This difference in redox behavior can be exploited to demonstrate in principle how high levels of enantiomeric excess in a mixture...
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| Published in | Journal of the American Chemical Society Vol. 132; no. 26; pp. 8903 - 8905 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
07.07.2010
Amer Chemical Soc |
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| Abstract | A chiral ferrocene-based boronic acid interacts with (R)- and (S)-Binol to form two complexes that exhibit significantly different ferrocene-based electrode potentials. This difference in redox behavior can be exploited to demonstrate in principle how high levels of enantiomeric excess in a mixture of enantiomers can be quantified and read-out using an electrochemical method. |
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| AbstractList | A chiral ferrocene-based boronic acid interacts with (R)- and (S)-Binol to form two complexes that exhibit significantly different ferrocene-based electrode potentials. This difference in redox behavior can be exploited to demonstrate in principle how high levels of enantiomeric excess in a mixture of enantiomers can be quantified and read-out using an electrochemical method. |
| Author | Mirri, Giorgio Bull, Steven D Tucker, James H. R Horton, Peter N Male, Louise James, Tony D |
| Author_xml | – sequence: 1 givenname: Giorgio surname: Mirri fullname: Mirri, Giorgio – sequence: 2 givenname: Steven D surname: Bull fullname: Bull, Steven D – sequence: 3 givenname: Peter N surname: Horton fullname: Horton, Peter N – sequence: 4 givenname: Tony D surname: James fullname: James, Tony D – sequence: 5 givenname: Louise surname: Male fullname: Male, Louise – sequence: 6 givenname: James H. R surname: Tucker fullname: Tucker, James H. R email: j.tucker@bham.ac.uk |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20536177$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja9060646 10.1002/asia.200800069 10.1021/ac025635q 10.1021/jo701809b 10.1016/j.ccr.2007.02.001 10.1039/b207643h 10.1002/anie.200500527 10.1021/ja803453e 10.1021/cr040700c 10.1038/nprot.2007.524 10.1002/elan.200804382 10.1039/b701796k 10.1021/ic800099j 10.1002/chir.20605 10.1002/anie.200904889 10.1039/b817800c 10.1002/chem.200900593 10.1021/jo8019187 10.1039/a804251i 10.1002/chem.200900878 10.1021/ja055817c 10.1039/b822685g 10.1002/ejic.200800474 10.1021/ja803806c 10.1021/ac061587o 10.1002/anie.200704346 10.2174/092986709788682173 10.1039/c39950001771 10.3390/s6060593 10.1016/S1359-6446(02)02436-4 10.1039/B207643H 10.1039/9781847557612 |
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| References | JAMES TD (WOS:000279561200041.12) 2006 Trojanowicz, M (WOS:000264063500002) 2009; 21 Casas-Solvas, JM (WOS:000269231800009) 2009; 15 Duddeck, H (WOS:000261782900009) 2009; 21 Woods, JE (WOS:000258080600018) 2008; 130 Nijhuis, CA (WOS:000248268500014) 2007; 251 Curiel, D (WOS:000268845000004) 2009; 15 Kurzawski, P (WOS:000252651200018) 2008; 47 Farina, V (WOS:000238973000007) 2006; 106 Molina, P (WOS:000258681100001) 2008 Bayly, SR (WOS:000247349800018) 2007 Traverse, JF (WOS:000178338600008) 2002; 7 ORI, A (WOS:A1995RU09200030) 1995 Zhang, X (WOS:000272207300073) 2009; 131 Nunez, MC (WOS:000267014800007) 2009; 16 Liu, HL (WOS:000274262800026) 2010; 49 Kataky, R (WOS:000264023500012) 2009 Moon, LS (WOS:000263453700018) 2009 Perez-Fuertes, Y (WOS:000254137000007) 2008; 3 Fujita, N (WOS:000257621100001) 2008; 3 Abbott, AP (WOS:000177502700009) 2002; 74 Arimori, S (WOS:000178537100039) 2002 Tucker, JHR (WOS:000175855100002) 2002; 31 Leung, D (WOS:000259139900044) 2008; 130 Zhu, L (WOS:000234941100047) 2006; 128 Willener, Y (WOS:000253152700006) 2008; 73 Bresner, C (WOS:000229708400026) 2005; 44 Amendola, V (WOS:000256255000050) 2008; 47 Yeste, SL (WOS:000262004000054) 2009; 74 Shahgaldian, P (WOS:000239555800004) 2006; 6 Chun, KM (WOS:000241670000048) 2006; 78 Moon L. S. (ref3/cit3b) 2009 Chun K. (ref5/cit5b) 2006; 78 ref9/cit9 ref6/cit6 Willener Y. (ref5/cit5a) 2008; 73 James T. D. (ref8/cit8a) 2006 ref11/cit11 Perez-Fuertes Y. (ref3/cit3d) 2008; 3 Fujita N. (ref8/cit8b) 2008; 3 Arimori S. (ref5/cit5d) 2002 Shahgaldian P. (ref7/cit7d) 2006; 6 Amendola V. (ref4/cit4b) 2008; 47 Kataky R. (ref7/cit7b) 2009 Nunez M. C. (ref1/cit1a) 2009; 16 Traverse J. F. (ref2/cit2) 2002; 7 ref5/cit5 Molina P. (ref4/cit4c) 2008 Zhu L. (ref9/cit9a) 2006; 128 Yeste S. L. (ref3/cit3c) 2009; 74 Abbott A. P. (ref5/cit5c) 2002; 74 Farina V. (ref1/cit1b) 2006; 106 Bresner C. (ref4/cit4e) 2005; 44 Ori A. (ref5/cit5e) 1995 Nijhuis C. A. (ref11/cit11c) 2007; 251 Leung D. (ref6/cit6d) 2008; 130 Woods J. E. (ref11/cit11b) 2008; 130 Duddeck H. (ref3/cit3a) 2009; 21 Trojanowicz M. (ref7/cit7a) 2009; 21 Bayly S. R. (ref4/cit4d) 2007 Casas-Solvas J. M. (ref4/cit4a) 2009; 15 Curiel D. (ref11/cit11a) 2009; 15 Tucker J. H. R. (ref11/cit11d) 2002; 31 ref4/cit4 Liu H. L. (ref6/cit6a) 2010; 49 Kurzawski P. (ref7/cit7c) 2008; 47 ref6/cit6c Zhang X. (ref6/cit6b) 2009; 131 ref7/cit7 |
| References_xml | – volume: 131 start-page: 17452 year: 2009 ident: WOS:000272207300073 article-title: Rational Design of d-PeT Phenylethynylated-Carbazole Monoboronic Acid Fluorescent Sensors for the Selective Detection of alpha-Hydroxyl Carboxylic Acids and Monosaccharides publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja9060646 contributor: fullname: Zhang, X – volume: 3 start-page: 1076 year: 2008 ident: WOS:000257621100001 article-title: Boronic acids in molecular self-assembly publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.200800069 contributor: fullname: Fujita, N – volume: 74 start-page: 4002 year: 2002 ident: WOS:000177502700009 article-title: Electrochemical recognition of chiral species using quaternary ammonium binaphthyl salts publication-title: ANALYTICAL CHEMISTRY doi: 10.1021/ac025635q contributor: fullname: Abbott, AP – volume: 73 start-page: 1225 year: 2008 ident: WOS:000253152700006 article-title: An exploration of ferrocenyl ureas as enantioselective electrochemical sensors for chiral carboxylate anions publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo701809b contributor: fullname: Willener, Y – volume: 251 start-page: 1761 year: 2007 ident: WOS:000248268500014 article-title: Electrochemically controlled supramolecular systems publication-title: COORDINATION CHEMISTRY REVIEWS doi: 10.1016/j.ccr.2007.02.001 contributor: fullname: Nijhuis, CA – start-page: 2368 year: 2002 ident: WOS:000178537100039 article-title: A modular electrochemical sensor for saccharides publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b207643h contributor: fullname: Arimori, S – volume: 44 start-page: 3606 year: 2005 ident: WOS:000229708400026 article-title: Selective electrochemical detection of hydrogen fluoride by ambiphilic ferrocene derivatives publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200500527 contributor: fullname: Bresner, C – volume: 130 start-page: 10070 year: 2008 ident: WOS:000258080600018 article-title: Electrochemically controlled hydrogen bonding. Electrolyte effects in an oxidation-based arylurea-amide system publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja803453e contributor: fullname: Woods, JE – volume: 106 start-page: 2734 year: 2006 ident: WOS:000238973000007 article-title: Asymmetric synthesis of active pharmaceutical ingredients publication-title: CHEMICAL REVIEWS doi: 10.1021/cr040700c contributor: fullname: Farina, V – volume: 3 start-page: 210 year: 2008 ident: WOS:000254137000007 article-title: Simple protocols for NMR analysis of the enantiomeric purity of chiral primary amines publication-title: NATURE PROTOCOLS doi: 10.1038/nprot.2007.524 contributor: fullname: Perez-Fuertes, Y – volume: 21 start-page: 229 year: 2009 ident: WOS:000264063500002 article-title: Electrochemical Chiral Sensors and Biosensors publication-title: ELECTROANALYSIS doi: 10.1002/elan.200804382 contributor: fullname: Trojanowicz, M – start-page: 2234 year: 2007 ident: WOS:000247349800018 article-title: Anion templated surface assembly of a redox-active sensory rotaxane publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b701796k contributor: fullname: Bayly, SR – volume: 47 start-page: 4808 year: 2008 ident: WOS:000256255000050 article-title: Redox active cage for the electrochemical sensing of anions publication-title: INORGANIC CHEMISTRY doi: 10.1021/ic800099j contributor: fullname: Amendola, V – volume: 21 start-page: 51 year: 2009 ident: WOS:000261782900009 article-title: Chiral Recognition of Ethers by NMR Spectroscopy publication-title: CHIRALITY doi: 10.1002/chir.20605 contributor: fullname: Duddeck, H – volume: 49 start-page: 602 year: 2010 ident: WOS:000274262800026 article-title: Highly Enantioselective Recognition of Structurally Diverse alpha-Hydroxycarboxylic Acids using a Fluorescent Sensor publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200904889 contributor: fullname: Liu, HL – start-page: 1067 year: 2009 ident: WOS:000263453700018 article-title: A new chiral shift reagent for the determination of enantiomeric excess and absolute configuration in cyanohydrins publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b817800c contributor: fullname: Moon, LS – volume: 7 start-page: 1002 year: 2002 ident: WOS:000178338600008 article-title: High-throughput methods for the development of new catalytic asymmetric reactions publication-title: DRUG DISCOVERY TODAY contributor: fullname: Traverse, JF – volume: 15 start-page: 8146 year: 2009 ident: WOS:000269231800009 article-title: Ferrocene-beta-Cyclodextrin Conjugates: Synthesis, Supramolecular Behavior, and Use as Electrochemical Sensors publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200900593 contributor: fullname: Casas-Solvas, JM – volume: 74 start-page: 427 year: 2009 ident: WOS:000262004000054 article-title: Simple Chiral Derivatization Protocols for H-1 NMR and F-19 NMR Spectroscopic Analysis of the Enantiopurity of Chiral Diols publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo8019187 contributor: fullname: Yeste, SL – volume: 31 start-page: 147 year: 2002 ident: WOS:000175855100002 article-title: Recent developments in the redox-switched binding of organic compounds publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/a804251i contributor: fullname: Tucker, JHR – volume: 15 start-page: 7534 year: 2009 ident: WOS:000268845000004 article-title: Electrochemically Induced Intermolecular Anion Transfer publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200900878 contributor: fullname: Curiel, D – volume: 128 start-page: 1222 year: 2006 ident: WOS:000234941100047 article-title: A structural investigation of the N-B interaction in an o-(N,N-dialkylaminomethyl)arylboronate system publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja055817c contributor: fullname: Zhu, L – start-page: 1490 year: 2009 ident: WOS:000264023500012 article-title: Chiral detection at a liquid-liquid interface publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b822685g contributor: fullname: Kataky, R – start-page: 3401 year: 2008 ident: WOS:000258681100001 article-title: Ferrocene-based small molecules for multichannel molecular recognition of cations and anions publication-title: EUROPEAN JOURNAL OF INORGANIC CHEMISTRY doi: 10.1002/ejic.200800474 contributor: fullname: Molina, P – volume: 6 start-page: 593 year: 2006 ident: WOS:000239555800004 article-title: Cyclodextrin derivatives as chiral supramolecular receptors for enantioselective sensing publication-title: SENSORS contributor: fullname: Shahgaldian, P – volume: 16 start-page: 2064 year: 2009 ident: WOS:000267014800007 article-title: Homochiral Drugs: A Demanding Tendency of the Pharmaceutical Industry publication-title: CURRENT MEDICINAL CHEMISTRY contributor: fullname: Nunez, MC – volume: 130 start-page: 12318 year: 2008 ident: WOS:000259139900044 article-title: Using enantioselective indicator displacement assays to determine the enantiomeric excess of alpha-amino acids publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja803806c contributor: fullname: Leung, D – start-page: 1771 year: 1995 ident: WOS:A1995RU09200030 article-title: ELECTROCHEMICAL DETECTION OF SACCHARIDES BY THE REDOX CYCLE OF A CHIRAL FERROCENYLBORONIC ACID-DERIVATIVE - A NOVEL METHOD FOR SUGAR SENSING publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: ORI, A – volume: 78 start-page: 7597 year: 2006 ident: WOS:000241670000048 article-title: Structure-selective recognition by voltammetry: Enantiomeric determination of amines using azophenolic crowns in aprotic solvent publication-title: ANALYTICAL CHEMISTRY doi: 10.1021/ac061587o contributor: fullname: Chun, KM – year: 2006 ident: WOS:000279561200041.12 publication-title: MONOGRAPHS SUPRAMOLE contributor: fullname: JAMES TD – volume: 47 start-page: 913 year: 2008 ident: WOS:000252651200018 article-title: Opposite signs of capacitive microsensor signals upon exposure to the enantiomers of methyl propionate compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200704346 contributor: fullname: Kurzawski, P – start-page: 3401 year: 2008 ident: ref4/cit4c publication-title: Eur. J. Inorg. Chem. doi: 10.1002/ejic.200800474 contributor: fullname: Molina P. – volume: 16 start-page: 2064 year: 2009 ident: ref1/cit1a publication-title: Curr. Med. Chem. doi: 10.2174/092986709788682173 contributor: fullname: Nunez M. C. – ident: ref9/cit9 – volume: 47 start-page: 4808 year: 2008 ident: ref4/cit4b publication-title: Inorg. Chem. doi: 10.1021/ic800099j contributor: fullname: Amendola V. – volume: 3 start-page: 1076 year: 2008 ident: ref8/cit8b publication-title: Chem. Asian. J. doi: 10.1002/asia.200800069 contributor: fullname: Fujita N. – ident: ref6/cit6c – start-page: 1771 year: 1995 ident: ref5/cit5e publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39950001771 contributor: fullname: Ori A. – ident: ref4/cit4 – volume: 74 start-page: 4002 year: 2002 ident: ref5/cit5c publication-title: Anal. Chem. doi: 10.1021/ac025635q contributor: fullname: Abbott A. P. – volume: 6 start-page: 593 year: 2006 ident: ref7/cit7d publication-title: Sensors doi: 10.3390/s6060593 contributor: fullname: Shahgaldian P. – volume: 7 start-page: 1002 year: 2002 ident: ref2/cit2 publication-title: Drug Discovery Today doi: 10.1016/S1359-6446(02)02436-4 contributor: fullname: Traverse J. F. – start-page: 2368 year: 2002 ident: ref5/cit5d publication-title: Chem. Commun. doi: 10.1039/B207643H contributor: fullname: Arimori S. – ident: ref6/cit6 – volume: 131 start-page: 17452 year: 2009 ident: ref6/cit6b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja9060646 contributor: fullname: Zhang X. – ident: ref11/cit11 – volume: 15 start-page: 7534 year: 2009 ident: ref11/cit11a publication-title: Chem. Eur. J. doi: 10.1002/chem.200900878 contributor: fullname: Curiel D. – volume: 130 start-page: 10070 year: 2008 ident: ref11/cit11b publication-title: J. Am. Chem. Soc. doi: 10.1021/ja803453e contributor: fullname: Woods J. E. – volume: 128 start-page: 1222 year: 2006 ident: ref9/cit9a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja055817c contributor: fullname: Zhu L. – volume: 44 start-page: 3606 year: 2005 ident: ref4/cit4e publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200500527 contributor: fullname: Bresner C. – volume: 74 start-page: 427 year: 2009 ident: ref3/cit3c publication-title: J. Org. Chem. doi: 10.1021/jo8019187 contributor: fullname: Yeste S. L. – volume: 49 start-page: 602 year: 2010 ident: ref6/cit6a publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200904889 contributor: fullname: Liu H. L. – volume: 106 start-page: 2734 year: 2006 ident: ref1/cit1b publication-title: Chem. Rev. doi: 10.1021/cr040700c contributor: fullname: Farina V. – volume: 21 start-page: 51 year: 2009 ident: ref3/cit3a publication-title: Chirality doi: 10.1002/chir.20605 contributor: fullname: Duddeck H. – start-page: 1067 year: 2009 ident: ref3/cit3b publication-title: Chem. Commun. doi: 10.1039/b817800c contributor: fullname: Moon L. S. – volume: 3 start-page: 210 year: 2008 ident: ref3/cit3d publication-title: Nat. Protoc. doi: 10.1038/nprot.2007.524 contributor: fullname: Perez-Fuertes Y. – start-page: 1490 year: 2009 ident: ref7/cit7b publication-title: Chem. Commun. doi: 10.1039/b822685g contributor: fullname: Kataky R. – volume: 73 start-page: 1225 year: 2008 ident: ref5/cit5a publication-title: J. Org. Chem. doi: 10.1021/jo701809b contributor: fullname: Willener Y. – ident: ref5/cit5 – volume: 15 start-page: 8146 year: 2009 ident: ref4/cit4a publication-title: Chem. Eur. J. doi: 10.1002/chem.200900593 contributor: fullname: Casas-Solvas J. M. – start-page: 2234 year: 2007 ident: ref4/cit4d publication-title: Chem. Commun. doi: 10.1039/b701796k contributor: fullname: Bayly S. R. – volume: 21 start-page: 229 year: 2009 ident: ref7/cit7a publication-title: Electroanalysis doi: 10.1002/elan.200804382 contributor: fullname: Trojanowicz M. – volume: 130 start-page: 12318 year: 2008 ident: ref6/cit6d publication-title: J. Am. Chem. Soc. doi: 10.1021/ja803806c contributor: fullname: Leung D. – volume: 31 start-page: 147 year: 2002 ident: ref11/cit11d publication-title: Chem. Soc. Rev. doi: 10.1039/a804251i contributor: fullname: Tucker J. H. R. – volume: 47 start-page: 913 year: 2008 ident: ref7/cit7c publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200704346 contributor: fullname: Kurzawski P. – volume: 78 start-page: 7597 year: 2006 ident: ref5/cit5b publication-title: Anal. Chem. doi: 10.1021/ac061587o contributor: fullname: Chun K. – ident: ref7/cit7 – volume: 251 start-page: 1761 year: 2007 ident: ref11/cit11c publication-title: Coord. Chem. Rev. doi: 10.1016/j.ccr.2007.02.001 contributor: fullname: Nijhuis C. A. – volume-title: Boronic acids in saccharide recognition year: 2006 ident: ref8/cit8a doi: 10.1039/9781847557612 contributor: fullname: James T. D. |
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| Snippet | A chiral ferrocene-based boronic acid interacts with (R)- and (S)-Binol to form two complexes that exhibit significantly different ferrocene-based electrode... A chiral ferrocene-based boronic acid interacts with (R)- and (S)-Binol to form two complexes that exhibit significantly different. ferrocene-based electrode... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Electrochemical Method for the Determination of Enantiomeric Excess of Binol Using Redox-Active Boronic Acids as Chiral Sensors |
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