Vayá Pérez, I.; Bueno Alejo, CJ.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2008). Determination of enantiomeric compositions by transient absorption spectroscopy using proteins as chiral selectors. Chemistry - A European Journal. 14(36):11284-11287. https://doi.org/10.1002/chem.200801657

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/96942

Ficheros en el ítem

Nombre: MS chem.200801657 ...

Tamaño: 253.0Kb

Formato: PDF

Descripción: Versión del Autor.

Abrir/Preview

Nombre: Chem Eur J_Publis ...

Tamaño: 346.4Kb

Formato: PDF

Descripción: Versión editorial

Solicitar una copia al autor

Metadatos del ítem

Título:	Determination of enantiomeric compositions by transient absorption spectroscopy using proteins as chiral selectors
Autor:	Vayá Pérez, Ignacio Bueno Alejo, Carlos Javier Jiménez Molero, María Consuelo Miranda Alonso, Miguel Ángel
Entidad UPV:	Universitat Politècnica de València. Departamento de Química - Departament de Química Universitat Politècnica de València. Instituto de Reconocimiento Molecular y Desarrollo Tecnológico - Institut de Reconeixement Molecular i Desenvolupament Tecnològic
Fecha difusión:	2008
Palabras clave:	Chiral resolution , Drugs , laser flash photolysis , Proteins , Stereoselective binding
Derechos de uso:	Reserva de todos los derechos
Fuente:	Chemistry - A European Journal. (issn: 0947-6539 )
DOI:	10.1002/chem.200801657
Editorial:	John Wiley & Sons
Versión del editor:	https://doi.org/10.1002/chem.200801657
Código del Proyecto:	info:eu-repo/grantAgreement/MEC//CTQ2007-67010/ES/ESPECIES TRANSITORIAS COMO HERRAMIENTAS EN QUIMICA BIOORGANICA/
Agradecimientos:	Financial support from the MEC (Grant CTQ2007-67010 and predoctoral fellowship to C.J.B. and I. V.), from the Carlos III Institute of Health (Grant RIRAAF, RETICS program) and from the Generalitat Valenciana (Prometeo ...[+] Financial support from the MEC (Grant CTQ2007-67010 and predoctoral fellowship to C.J.B. and I. V.), from the Carlos III Institute of Health (Grant RIRAAF, RETICS program) and from the Generalitat Valenciana (Prometeo Program) is gratefully acknowledged. [-]
Tipo:	Artículo

References

Finn, M. G. (2002). Emerging methods for the rapid determination of enantiomeric excess. Chirality, 14(7), 534-540. doi:10.1002/chir.10101

Maier, N. M., Franco, P., & Lindner, W. (2001). Separation of enantiomers: needs, challenges, perspectives. Journal of Chromatography A, 906(1-2), 3-33. doi:10.1016/s0021-9673(00)00532-x

Pirkle, W. H., & Finn, J. M. (1981). Chiral high-pressure liquid chromatographic stationary phases. 3. General resolution of arylalkylcarbinols. The Journal of Organic Chemistry, 46(14), 2935-2938. doi:10.1021/jo00327a019 [+]

Finn, M. G. (2002). Emerging methods for the rapid determination of enantiomeric excess. Chirality, 14(7), 534-540. doi:10.1002/chir.10101

Maier, N. M., Franco, P., & Lindner, W. (2001). Separation of enantiomers: needs, challenges, perspectives. Journal of Chromatography A, 906(1-2), 3-33. doi:10.1016/s0021-9673(00)00532-x

Pirkle, W. H., & Finn, J. M. (1981). Chiral high-pressure liquid chromatographic stationary phases. 3. General resolution of arylalkylcarbinols. The Journal of Organic Chemistry, 46(14), 2935-2938. doi:10.1021/jo00327a019

Okamoto, Y., & Yashima, E. (1998). Chromatographische Enantiomerentrennung an Polysaccharidderivaten. Angewandte Chemie, 110(8), 1072-1095. doi:10.1002/(sici)1521-3757(19980420)110:8<1072::aid-ange1072>3.0.co;2-q

Edkins, T. J., & Bobbitt, D. R. (2001). Peer Reviewed: Miniaturization of Enantioselective Detectors. Analytical Chemistry, 73(17), 488 A-496 A. doi:10.1021/ac0124991

Tsukamoto, M., & Kagan, H. B. (2002). Recent Advances in the Measurement of Enantiomeric Excesses. Advanced Synthesis & Catalysis, 344(5), 453. doi:10.1002/1615-4169(200207)344:5<453::aid-adsc453>3.0.co;2-u

Guo, J., Wu, J., Siuzdak, G., & Finn, M. G. (1999). Bestimmung von Enantiomerenüberschüssen durch kinetische Racematspaltung und Massenspektrometrie. Angewandte Chemie, 111(12), 1868-1871. doi:10.1002/(sici)1521-3757(19990614)111:12<1868::aid-ange1868>3.0.co;2-j

Guo, J., Wu, J., Siuzdak, G., & Finn, M. G. (1999). Measurement of Enantiomeric Excess by Kinetic Resolution and Mass Spectrometry. Angewandte Chemie International Edition, 38(12), 1755-1758. doi:10.1002/(sici)1521-3773(19990614)38:12<1755::aid-anie1755>3.0.co;2-q

Reetz, M. T., Becker, M. H., Klein, H.-W., & Stöckigt, D. (1999). Eine Methode zum High-Throughput-Screening von enantioselektiven Katalysatoren. Angewandte Chemie, 111(12), 1872-1875. doi:10.1002/(sici)1521-3757(19990614)111:12<1872::aid-ange1872>3.0.co;2-g

Reetz, M. T., Becker, M. H., Klein, H.-W., & Stöckigt, D. (1999). A Method for High-Throughput Screening of Enantioselective Catalysts. Angewandte Chemie International Edition, 38(12), 1758-1761. doi:10.1002/(sici)1521-3773(19990614)38:12<1758::aid-anie1758>3.0.co;2-8

Markert, C., & Pfaltz, A. (2004). Screening of Chiral Catalysts and Catalyst Mixtures by Mass Spectrometric Monitoring of Catalytic Intermediates. Angewandte Chemie, 116(19), 2552-2554. doi:10.1002/ange.200453844

Markert, C., & Pfaltz, A. (2004). Screening of Chiral Catalysts and Catalyst Mixtures by Mass Spectrometric Monitoring of Catalytic Intermediates. Angewandte Chemie International Edition, 43(19), 2498-2500. doi:10.1002/anie.200453844

Reetz, M. T., Kühling, K. M., Deege, A., Hinrichs, H., & Belder, D. (2000). Super-Hochdurchsatz-Screening von enantioselektiven Katalysatoren mittels parallelisierter Kapillarelektrophorese. Angewandte Chemie, 112(21), 4049-4052. doi:10.1002/1521-3757(20001103)112:21<4049::aid-ange4049>3.0.co;2-n

Reetz, M. T., Kühling, K. M., Deege, A., Hinrichs, H., & Belder, D. (2000). Super-High-Throughput Screening of Enantioselective Catalysts by Using Capillary Array Electrophoresis. Angewandte Chemie, 39(21), 3891-3893. doi:10.1002/1521-3773(20001103)39:21<3891::aid-anie3891>3.0.co;2-1

Abato, P., & Seto, C. T. (2001). EMDee:  An Enzymatic Method for Determining Enantiomeric Excess. Journal of the American Chemical Society, 123(37), 9206-9207. doi:10.1021/ja016177q

Van Delden, R. A., & Feringa, B. L. (2001). Color Indicators of Molecular Chirality Based on Doped Liquid Crystals. Angewandte Chemie, 113(17), 3298-3300. doi:10.1002/1521-3757(20010903)113:17<3298::aid-ange3298>3.0.co;2-e

Van Delden, R. A., & Feringa, B. L. (2001). Color Indicators of Molecular Chirality Based on Doped Liquid Crystals. Angewandte Chemie International Edition, 40(17), 3198-3200. doi:10.1002/1521-3773(20010903)40:17<3198::aid-anie3198>3.0.co;2-i

Taran, F., Gauchet, C., Mohar, B., Meunier, S., Valleix, A., Renard, P. Y., … Mioskowski, C. (2002). High-Throughput Screening of Enantioselective Catalysts by Immunoassay. Angewandte Chemie, 114(1), 132-135. doi:10.1002/1521-3757(20020104)114:1<132::aid-ange132>3.0.co;2-d

Taran, F., Gauchet, C., Mohar, B., Meunier, S., Valleix, A., Renard, P. Y., … Mioskowski, C. (2002). High-Throughput Screening of Enantioselective Catalysts by Immunoassay. Angewandte Chemie International Edition, 41(1), 124-127. doi:10.1002/1521-3773(20020104)41:1<124::aid-anie124>3.0.co;2-r

Li, Z., Bütikofer, L., & Witholt, B. (2004). High-Throughput Measurement of the Enantiomeric Excess of Chiral Alcohols by Using Two Enzymes. Angewandte Chemie, 116(13), 1730-1734. doi:10.1002/ange.200353055

Li, Z., Bütikofer, L., & Witholt, B. (2004). High-Throughput Measurement of the Enantiomeric Excess of Chiral Alcohols by Using Two Enzymes. Angewandte Chemie International Edition, 43(13), 1698-1702. doi:10.1002/anie.200353055

Eelkema, R., van Delden, R. A., & Feringa, B. L. (2004). Direct Visual Detection of the Stereoselectivity of a Catalytic Reaction. Angewandte Chemie, 116(38), 5123-5126. doi:10.1002/ange.200460822

Eelkema, R., van Delden, R. A., & Feringa, B. L. (2004). Direct Visual Detection of the Stereoselectivity of a Catalytic Reaction. Angewandte Chemie International Edition, 43(38), 5013-5016. doi:10.1002/anie.200460822

Dey, S., Karukurichi, K. R., Shen, W., & Berkowitz, D. B. (2005). Double-Cuvette ISES:  In Situ Estimation of Enantioselectivity and Relative Rate for Catalyst Screening. Journal of the American Chemical Society, 127(24), 8610-8611. doi:10.1021/ja052010b

Mei, X., & Wolf, C. (2006). Determination of Enantiomeric Excess and Concentration of Unprotected Amino Acids, Amines, Amino Alcohols, and Carboxylic Acids by Competitive Binding Assays with a Chiral Scandium Complex. Journal of the American Chemical Society, 128(41), 13326-13327. doi:10.1021/ja0636486

Reetz, M. T., Becker, M. H., Kühling, K. M., & Holzwarth, A. (1998). Zeitaufgelöste IR-thermographische Detektion und Screening von enantioselektiven katalytischen Reaktionen. Angewandte Chemie, 110(19), 2792-2795. doi:10.1002/(sici)1521-3757(19981002)110:19<2792::aid-ange2792>3.0.co;2-2

Reetz, M. T., Becker, M. H., Kühling, K. M., & Holzwarth, A. (1998). Time-Resolved IR-Thermographic Detection and Screening of Enantioselectivity in Catalytic Reactions. Angewandte Chemie International Edition, 37(19), 2647-2650. doi:10.1002/(sici)1521-3773(19981016)37:19<2647::aid-anie2647>3.0.co;2-i

Ding, K., Ishii, A., & Mikami, K. (1999). Super-High-Throughput-Screening chiraler Liganden und Aktivatoren: asymmetrische Aktivierung chiraler Diol-Zink-Katalysatoren durch chirale Stickstoffaktivatoren für die enantioselektive Addition von Diethylzink an Aldehyde. Angewandte Chemie, 111(4), 519-523. doi:10.1002/(sici)1521-3757(19990215)111:4<519::aid-ange519>3.0.co;2-6

Ding, K., Ishii, A., & Mikami, K. (1999). Super High Throughput Screening (SHTS) of Chiral Ligands and Activators: Asymmetric Activation of Chiral Diol-Zinc Catalysts by Chiral Nitrogen Activators for the Enantioselective Addition of Diethylzinc to Aldehydes. Angewandte Chemie International Edition, 38(4), 497-501. doi:10.1002/(sici)1521-3773(19990215)38:4<497::aid-anie497>3.0.co;2-g

Yannoni, C. S. (1982). High-resolution NMR in solids: the CPMAS experiment. Accounts of Chemical Research, 15(7), 201-208. doi:10.1021/ar00079a003

Tekely, P., Gardiennet, C., Potrzebowski, M. J., Sebald, A., Reichert, D., & Luz, Z. (2002). Probing molecular geometry of solids by nuclear magnetic resonance spin exchange at the n=0 rotational-resonance condition. The Journal of Chemical Physics, 116(17), 7607-7616. doi:10.1063/1.1465416

Potrzebowski, M. J., Tadeusiak, E., Misiura, K., Ciesielski, W., Bujacz, G., & Tekely, P. (2002). A New Method for Distinguishing between Enantiomers and Racemates and Assignment of Enantiomeric Purity by Means of Solid-State NMR. Examples from Oxazaphosphorinanes. Chemistry - A European Journal, 8(21), 5007-5011. doi:10.1002/1521-3765(20021104)8:21<5007::aid-chem5007>3.0.co;2-b

Evans, M. A., & Morken, J. P. (2002). Isotopically Chiral Probes for in Situ High-Throughput Asymmetric Reaction Analysis. Journal of the American Chemical Society, 124(31), 9020-9021. doi:10.1021/ja026703t

James, T. D., Samankumara Sandanayake, K. R. A., & Shinkai, S. (1995). Chiral discrimination of monosaccharides using a fluorescent molecular sensor. Nature, 374(6520), 345-347. doi:10.1038/374345a0

(s. f.). doi:10.1021/ja984139

Beer, G., Daub, J., & Rurack, K. (2001). Chiral discrimination with a fluorescent boron–dipyrromethene dye. Chemical Communications, (12), 1138-1139. doi:10.1039/b102376b

Zhao, J., Fyles, T. M., & James, T. D. (2004). Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar Acids. Angewandte Chemie, 116(26), 3543-3546. doi:10.1002/ange.200454033

Zhao, J., Fyles, T. M., & James, T. D. (2004). Chiral Binol–Bisboronic Acid as Fluorescence Sensor for Sugar Acids. Angewandte Chemie International Edition, 43(26), 3461-3464. doi:10.1002/anie.200454033

Pu, L. (2004). Fluorescence of Organic Molecules in Chiral Recognition. Chemical Reviews, 104(3), 1687-1716. doi:10.1021/cr030052h

Li, Z.-B., Lin, J., Qin, Y.-C., & Pu, L. (2005). Enantioselective Fluorescent Recognition of a Soluble «Supported» Chiral Acid:  Toward a New Method for Chiral Catalyst Screening. Organic Letters, 7(16), 3441-3444. doi:10.1021/ol0510163

Matsushita, M., Yoshida, K., Yamamoto, N., Wirsching, P., Lerner, R. A., & Janda, K. D. (2003). High-Throughput Screening by Using a Blue-Fluorescent Antibody Sensor. Angewandte Chemie, 115(48), 6166-6169. doi:10.1002/ange.200352793

Matsushita, M., Yoshida, K., Yamamoto, N., Wirsching, P., Lerner, R. A., & Janda, K. D. (2003). High-Throughput Screening by Using a Blue-Fluorescent Antibody Sensor. Angewandte Chemie International Edition, 42(48), 5984-5987. doi:10.1002/anie.200352793

Hamberg, A., Lundgren, S., Penhoat, M., Moberg, C., & Hult, K. (2006). High-Throughput Enzymatic Method for Enantiomeric Excess Determination of O-Acetylated Cyanohydrins. Journal of the American Chemical Society, 128(7), 2234-2235. doi:10.1021/ja058474r

Busch, K. W., Swamidoss, I. M., Fakayode, S. O., & Busch, M. A. (2003). Determination of the Enantiomeric Composition of Guest Molecules by Chemometric Analysis of the UV−Visible Spectra of Cyclodextrin Guest−Host Complexes. Journal of the American Chemical Society, 125(7), 1690-1691. doi:10.1021/ja025947a

Fakayode, S. O., Busch, M. A., Bellert, D. J., & Busch, K. W. (2005). Determination of the enantiomeric composition of phenylalanine samples by chemometric analysis of the fluorescence spectra of cyclodextrin guest–host complexes. The Analyst, 130(2), 233-241. doi:10.1039/b405478d

ABE, Y., YASUOKA, S., SHOJI, T., SUGATA, S., HATTORI, K., IWATA, K., & SUZUKI, H. (2002). Peculiar Chiral Discrimination of Bovine Serum Albumin to (.+-.)-N-Dansyl-norleucine. Analytical Sciences, 18(7), 823-825. doi:10.2116/analsci.18.823

Hamblin, J., Abboyi, N., & Lowe, M. P. (2005). A binaphthyl-containing Eu(iii) complex and its interaction with human serum albumin: a luminescence study. Chemical Communications, (5), 657. doi:10.1039/b415464a

Singh, S. S., & Mehta, J. (2006). Measurement of drug–protein binding by immobilized human serum albumin-HPLC and comparison with ultrafiltration. Journal of Chromatography B, 834(1-2), 108-116. doi:10.1016/j.jchromb.2006.02.053

Hödl, H., Koidl, J., Schmid, M. G., & Gübitz, G. (2006). Chiral resolution of tryptophan derivatives by CE using canine serum albumin and bovine serum albumin as chiral selectors. ELECTROPHORESIS, 27(23), 4755-4762. doi:10.1002/elps.200600425

Martínez-Gómez, M. A., Sagrado, S., Villanueva-Camañas, R. M., & Medina-Hernández, M. J. (2007). Enantioseparation of phenotiazines by affinity electrokinetic chromatography using human serum albumin as chiral selector. Analytica Chimica Acta, 582(2), 223-228. doi:10.1016/j.aca.2006.09.036

Jiménez, M. C., Miranda, M. A., & Vayá, I. (2005). Triplet Excited States as Chiral Reporters for the Binding of Drugs to Transport Proteins. Journal of the American Chemical Society, 127(29), 10134-10135. doi:10.1021/ja0514489

Vayá, I., Bueno, C. J., Jiménez, M. C., & Miranda, M. A. (2006). Use of Triplet Excited States for the Study of Drug Binding to Human and Bovine Serum Albumins. ChemMedChem, 1(9), 1015-1020. doi:10.1002/cmdc.200600061

Bohne, C., Barra, M., Boch, R., Abuin, E. B., & Scaiano, J. C. (1992). Excited triplet states as probes in organized systems. An overview of recent results. Journal of Photochemistry and Photobiology A: Chemistry, 65(1-2), 249-265. doi:10.1016/1010-6030(92)85050-5

Jiménez, M. C., Miranda, M. A., Tormos, R., & Vayá, I. (2004). Characterisation of the lowest singlet and triplet excited states of S-flurbiprofen. Photochem. Photobiol. Sci., 3(11-12), 1038-1041. doi:10.1039/b408530b

[-]

recommendations

 

Este ítem aparece en la(s) siguiente(s) colección(ones)

• Artículos, conferencias, monografías [48001]
  

Mostrar el registro completo del ítem