(+) or (-)-1-(9-fluorenyl)ethyl chloroformate as chiral derivatizing agent: A review.

[en] Over the last 30years, (+/-)-1-(9-fluorenyl)ethyl chloroformate ((+/-)-FLEC) was used as a chiral derivatizing agent in various analytical applications involving a wide range of endogenous, pharmaceutical and environmentally relevant molecules. This comprehensive review aims to present all the significant aspects related to the state of the art in FLEC labeling and subsequent chiral separation of the resulting diastereomers using LC, SFC and CE techniques.

Research Center/Unit :

CIRM - Centre Interdisciplinaire de Recherche sur le Médicament - ULiège

Disciplines :

Pharmacy, pharmacology & toxicology

Author, co-author :

Moldovan, Radu-Cristian

Bodoki, Ede

Servais, Anne-Catherine ; Université de Liège > Département de pharmacie > Analyse des médicaments

Crommen, Jacques ; Université de Liège > Département de pharmacie > Département de pharmacie

Oprean, Radu

Fillet, Marianne ; Université de Liège > Département de pharmacie > Analyse des médicaments

Language :

English

Title :

(+) or (-)-1-(9-fluorenyl)ethyl chloroformate as chiral derivatizing agent: A review.

Publication date :

2017

Journal title :

Journal of Chromatography. A

ISSN :

0021-9673

eISSN :

1873-3778

Publisher :

Elsevier, Amsterdam, Netherlands

Volume :

1513

Pages :

1-17

Peer reviewed :

Peer Reviewed verified by ORBi

Commentary :

Available on ORBi :

since 17 August 2017

Statistics

Number of views

112 (9 by ULiège)

Number of downloads

1 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

Einarsson, S., Josefsson, B., Möller, P., Sanchez, D., Separation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography. Anal. Chem. 59 (1987), 1191–1195, 10.1021/ac00135a025.
Fradi, I., Farcas, E., Ben Saïd, A., Yans, M.-L.L., Lamalle, C., Somsen, G.W., Prior, A., de Jong, G.J., Kallel, M., Crommen, J., Servais, A.-C., Fillet, M., In-capillary derivatization with (−)-1-(9-fluorenyl)ethyl chloroformate as chiral labeling agent for the electrophoretic separation of amino acids. J. Chromatogr. A 1363 (2014), 338–347, 10.1016/j.chroma.2014.07.022.
Moldovan, R.-C., Bodoki, E., Kacsó, T., Servais, A.-C., Crommen, J., Oprean, R., Fillet, M., A micellar electrokinetic chromatography?mass spectrometry approach using in-capillary diastereomeric derivatization for fully automatized chiral analysis of amino acids. J. Chromatogr. A 1467 (2016), 400–408, 10.1016/j.chroma.2016.08.035.
Davies, C.L., Chromatography of β-adrenergic blocking agents. J. Chromatogr. B Biomed. Sci. Appl. 531 (1990), 131–180, 10.1016/S0378-4347(00)82283-5.
Dyas, A.M., The chiral chromatographic separation of β-adrenoceptor blocking drugs. J. Pharm. Biomed. Anal. 10 (1992), 383–404, 10.1016/0731-7085(92)80057-T.
Bovingdon, M.E., Webster, R.A., Derivatization reactions for neurotransmitters and their automation. J. Chromatogr. B Biomed. Sci. Appl. 659 (1994), 157–183, 10.1016/0378-4347(94)00145-6.
Krull, I.S., Deyl, Z., Lingeman, H., General strategies and selection of derivatization reactions for liquid chromatography and capillary electrophoresis. J. Chromatogr. B Biomed. Sci. Appl. 659 (1994), 1–17, 10.1016/0378-4347(94)00151-0.
Imai, K., Fukushima, T., Santa, T., Homma, H., Hamase, K., Sakai, K., Kato, M., Analytical chemistry and biochemistry of D-amino acids. Biomed. Chromatogr. 10 (1996), 303–312, 10.1002/(SICI)1099-0801(199611)10:6<303:AID-BMC624 > 3.0.CO;2-B.
Toyo'oka, T., Recent progress in liquid chromatographic enantioseparation based upon diastereomer formation with fluorescent chiral derivatization reagents. Biomed. Chromatogr. 10 (1996), 265–277, 10.1002/(SICI)1099-0801(199611)10:6<265:AID-BMC602>3.0.CO;2-A.
Iida, T., Santa, T., Toriba, A., Imai, K., Amino acid sequence and D/L-configuration determination methods for D-amino acid-containing peptides in living organisms. Biomed. Chromatogr. 15 (2001), 319–327, 10.1002/bmc.80.
Sun, X.X., Sun, L.Z., Aboul-Enein, H.Y., Chiral derivatization reagents for drug enantioseparation by high-performance liquid chromatography based upon pre-column derivatization and formation of diastereomers: enantioselectivity and related structure. Biomed. Chromatogr. 15 (2001), 116–132, 10.1002/bmc.41.
Hamase, K., Morikawa, A., Zaitsu, K., D-Amino acids in mammals and their diagnostic value. J. Chromatogr. B 781 (2002), 73–91, 10.1016/S1570-0232(02)00690-6.
Fukushima, T., Usui, N., Santa, T., Imai, K., Recent progress in derivatization methods for LC and CE analysis. J. Pharm. Biomed. Anal. 30 (2003), 1655–1687, 10.1016/S0731-7085(02)00511-3.
Ilisz, I., Berkecz, R., Péter, A., Application of chiral derivatizing agents in the high-performance liquid chromatographic separation of amino acid enantiomers: a review. J. Pharm. Biomed. Anal. 47 (2008), 1–15, 10.1016/j.jpba.2007.12.013.
Waldhier, M.C., Gruber, M.A., Dettmer, K., Oefner, P.J., Capillary electrophoresis and column chromatography in biomedical chiral amino acid analysis. Anal. Bioanal. Chem. 394 (2009), 695–706, 10.1007/s00216-009-2792-y.
Kumar, A.P., Jin, D., Lee, Y.-I., Recent development on spectroscopic methods for chiral analysis of enantiomeric compounds. Appl. Spectrosc. Rev. 44 (2009), 267–316, 10.1080/05704920902717971.
Ilisz, I., Pataj, Z., Aranyi, A., Péter, A., High-Performance liquid chromatography of biologically important, small epimeric peptides and their L, D-amino acid content. Mini-Rev. Chem 10 (2010), 287–298, 10.2174/138955710791330981.
Miyoshi, Y., Koga, R., Oyama, T., Han, H., Ueno, K., Masuyama, K., Itoh, Y., Hamase, K., HPLC analysis of naturally occurring free D-amino acids in mammals. J. Pharm. Biomed. Anal. 69 (2012), 42–49, 10.1016/j.jpba.2012.01.041.
Ilisz, I., Aranyi, A., Pataj, Z., Péter, A., Enantiomeric separation of nonproteinogenic amino acids by high-performance liquid chromatography. J. Chromatogr. A 1269 (2012), 94–121, 10.1016/j.chroma.2012.07.011.
Ilisz, I., Aranyi, A., Péter, A., Chiral derivatizations applied for the separation of unusual amino acid enantiomers by liquid chromatography and related techniques. J. Chromatogr. A 1296 (2013), 119–139, 10.1016/j.chroma.2013.03.034.
Deyl, Z., Miksik, I., Tesarova, E., Selected derivatization reactions. Deyl, Z., Miksik, I., Tagliaro, F., Tesarova, E., (eds.) Advanced Chromatographic and Electromigration Methods in Biosciences, 1998, Elsevier B.V., 141–196.
Josefsson, B., HPLC of amino acids as chloroformate derivatives. Molnár-Perl, I., (eds.) Quantitation of Amino Acids and Amines by Chromatography, 2005, Elsevier B.V., 199–228.
Camerino, M.A., Chalmers, D.K., Thompson, P.E., (+)-Fluorenylethylchloroformate (FLEC) −improved synthesis for application in chiral analysis and peptidomimetic synthesis. Org. Biomol. Chem., 11, 2013, 2571, 10.1039/c3ob40218e.
Vogt, C., Georgi, A., Werner, G., Enantiomeric separation of D/L-carnitine using HPLC and CZE after derivatization. Chromatographia 40 (1995), 287–295, 10.1007/BF02290359.
Engström, A., Wan, H., Andersson, P.E., Josefsson, B., Determination of chiral reagent purity by capillary electrophoresis. J. Chromatogr. A 715 (1995), 151–158, 10.1016/0021-9673(95)00588-E.
Okuma, E., Abe, H., Simultaneous determination of d- and l-amino acids in the nervous tissues of crustaceans using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase ion-pair high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl. 660 (1994), 243–250, 10.1016/0378-4347(94)00304-1.
Bergqvist, Y., Doverskog, M., Al Kabbani, J., High-performance liquid chromatographic determination of (SR)- and (RS)-enantiomers of mefloquine in plasma and capillary blood sampled on paper after derivatization with (−)-1-(9-fluorenyl)ethyl chloroformate. J. Chromatogr. B Biomed. Sci. Appl. 652 (1994), 73–81, 10.1016/0378-4347(93)E0386-5.
Hutchaleelaha, A., Walters, A., Chow, H.-H., Mayersohn, M., Sensitive enantiomer-specific high-performance liquid chromatographic analysis of methamphetamine and amphetamine from serum using precolumn fluorescent derivatization. J. Chromatogr. B Biomed. Sci. Appl. 658 (1994), 103–112, 10.1016/0378-4347(94)00229-0.
Fransson, B., Ragnarsson, U., Separation of enantiomers of α-hydroxy acids by reversed-phase liquid chromatography after derivatization with 1-(9-fluorenyl)ethyl chloroformate. J. Chromatogr. A 827 (1998), 31–36, 10.1016/S0021-9673(98)00770-5.
Lai, F., Mayer, A., Sheehan, T., Chiral separation and detection enhancement of propranolol using automated pre-column derivatization. J. Pharm. Biomed. Anal. 11 (1993), 117–120, 10.1016/0731-7085(93)80131-J.
Freimüller, S., Altorfer, H., A chiral HPLC method for the determination of low amounts of d-carnitine in l-carnitine after derivatization with (+)-FLEC. J. Pharm. Biomed. Anal. 30 (2002), 209–218, 10.1016/S0731-7085(02)00341-2.
Boursier-Neyret, C., Baune, A., Klippert, P., Castagne, I., Sauveur, C., Determination of S 12024 enantiomers in human plasma by liquid chromatography after chiral pre-column derivatization. J. Pharm. Biomed. Anal. 11 (1993), 1161–1166, 10.1016/0731-7085(93)80099-M.
Chen, Y.-P., Hsu, M.-C., Sheng Chien, C., Analysis of forensic samples using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and liquid chromatography with fluorimetric detection. J. Chromatogr. A 672 (1994), 135–140, 10.1016/0021-9673(94)80601-2.
De Witt, P., Deias, R., Muck, S., Galletti, B., Meloni, D., Celletti, P., Marzo, A., High-performance liquid chromatography and capillary electrophoresis of L- and D-carnitine by precolumn diastereomeric derivatization. J. Chromatogr. B Biomed. Sci. Appl. 657 (1994), 67–73, 10.1016/0378-4347(94)80071-5.
Vogt, C., Kiessig, S., Separation of d/l-carnitine enatiomers by capillary electrophoresis. J. Chromatogr. A 745 (1996), 53–60, 10.1016/0021-9673(96)00384-6.
Sukbuntherng, J., Hutchaleelaha, A., Chow, H.-H., Mayersohn, M., Separation and quantitation of the enantiomers of methamphetamine and its metabolites in urine by HPLC: precolumn derivatization and fluorescence detection. J. Anal. Toxicol. 19 (1995), 139–147, 10.1093/jat/19.3.139.
Campíns-Falcó, P., Verdú-Andrés, J., Herráez-Hernández, R., Separation of the enantiomers of primary and secondary amphetamines by liquid chromatography after derivatization with (−)-1-(9-fluorenyl)ethyl chloroformate. Chromatographia 57 (2003), 309–316, 10.1007/BF02492401.
Walters, R.R., Buist, S.C., Improved enantioselective method for the determination of the enantiomers of reboxetine in plasma by solid-phase extraction, chiral derivatization, and column-switching high-performance liquid chromatography with fluorescence detection. J. Chromatogr. A 828 (1998), 167–176, 10.1016/S0021-9673(98)00664-5.
Frigerio, E., Pianezzola, E., Benedetti, M.S., Sensitive procedure for the determination of reboxetine enantiomers in human plasma by reversed-phase high-performance liquid chromatography with fluorimetric detection after chiral derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate. J. Chromatogr. A 660 (1994), 351–358, 10.1016/0021-9673(94)85130-1.
Witte, D.T., Ahnoff, M., Karlsson, K.-E., Franke, J.-P., de Zeeuw, R.A., Liquid chromatographic chiral separations of the N-6-(endo-2-norbornyl)-9-methyladenine enantiomers. J. Chromatogr. A 641 (1993), 39–48, 10.1016/0021-9673(93)83456-3.
Molnár-Perl, I., Advancement in the derivatizations of the amino groups with the o-phthaldehyde-thiol and with the 9-fluorenylmethyloxycarbonyl chloride reagents. J. Chromatogr. B 879 (2011), 1241–1269, 10.1016/j.jchromb.2011.01.027.
Hori, Y., Fujisawa, M., Shimada, K., Sato, M., Honda, M., Hirose, Y., Enantioselective analysis of glufosinate using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate and reversed-phase liquid chromatography. J. Chromatogr. B 776 (2002), 191–198, 10.1016/S1570-0232(02)00351-3.
Veuthey, J.L., Caude, M., Rosset, R., Separation of some amino acids by supercritical fluid chromatography after a pre-derivatization step with classical reagents. Chromatographia 27 (1989), 105–108, 10.1007/BF02265859.
Prior, A., Moldovan, R.C., Crommen, J., Servais, A.C., Fillet, M., de Jong, G.J., Somsen, G.W., Enantioselective capillary electrophoresis-mass spectrometry of amino acids in cerebrospinal fluid using a chiral derivatizing agent and volatile surfactant. Anal. Chim. Acta 940 (2016), 150–158, 10.1016/j.aca.2016.08.040.
Verdú-Andrés, J., Campíns-Falcó, P., Herráez-Hernández, R., Enantioselective analysis of amphetamine-Related designer drugs in body fluids using liquid chromatography and solid-Phase derivatization. Chromatographia 60 (2004), 537–544, 10.1365/s10337-004-0411-9.
Zoutendam, P.H., Canty, J.F., Martin, M.J., Dirr, M.K., Development of a chiral assay for a novel, nonfluorinated quinolone, PGE-9509924, in dog plasma using high performance liquid chromatography with electrospray tandem mass spectrometry or fluorescence detection. J. Pharm. Biomed. Anal. 30 (2002), 1–11, 10.1016/S0731-7085(01)00717-8.
Brückner, H., Haasmann, S., Langer, M., Westhauser, T., Wittner, R., Godel, H., Liquid chromatographic determination of D- and L-amino acids by derivatization with o-phthaldialdehyde and chiral thiols. Applications with reference to biosciences. J. Chromatogr. A 666 (1994), 259–273, 10.1016/0021-9673(94)80388-9.
Houben, R.J.H., Gielen, H., van der Wal, S., Automated preseparation derivatization on a capillary electrophoresis instrument. J. Chromatogr. A 634 (1993), 317–322, 10.1016/0021-9673(93)83019-O.
Shimada, K., Mitamura, K., Morita, M., Hirakata, K., Separation of the diastereomers of baclofen by high performance liquid chromatography using cyclodextrin as a mobile phase additive. J. Liq. Chromatogr. 16 (1993), 3311–3320, 10.1080/10826079308019650.
Wan, H., Andersson, P.E., Engström, A., Blomberg, L.G., Direct and indirect chiral separation of amino acids by capillary electrophoresis. J. Chromatogr. A 704 (1995), 179–193, 10.1016/0021-9673(95)00146-E.
Chan, K.C., Muschik, G.M., Issaq, H.J., Enantiomeric separation of amino acids using micellar electrokinetic chromatography after pre-column derivatization with the chiral reagent 1-(9-fluorenyl)-ethyl chloroformate. Electrophoresis 16 (1995), 504–509, 10.1002/elps.1150160183.
Okuma, E., Watanabe, K., Abe, H., Distribution of free D-amino acids in bivalve mollusks and the effects of physiological conditions on the levels of D-and L-alanine in the tissues of the hard clam, Meretrix lusoria. Fish. Sci. 64 (1998), 606–611, 10.2331/fishsci.64.606.
Okama, E., Abe, H., Effects of starvation and D- or L-alanine administration on the free D- and L-alanine levels in the muscle and hepatopancreas of the crayfish, Procambarus clarkii. Comp. Biochem. Physiol. Part A Mol. Integr. Physiol. 120 (1998), 681–686, 10.1016/S1095-6433(98)10086-7.
Abe, H., Okuma, E., Amano, H., Noda, H., Watanabe, K., Role of free D- and L-alanine in the Japanese mitten crab Eriocheir japonicus to intracellular osmoregulation during downstream spawning migration. Comp. Biochem. Physiol. Part A Mol. Integr. Physiol. 123 (1999), 55–59, 10.1016/S1095-6433(99)00037-9.
Abe, H., Okuma, E., Amano, H., Noda, H., Watanabe, K., Effects of seawater acclimation on the levels of free D- and L-alanine and other osmolytes in the Japanese mitten crab Eriocheir Japonicus. Fish. Sci. 65 (1999), 949–954, 10.2331/fishsci.65.949.
Todoroki, N., Shibata, K., Yamada, T., Kera, Y., Yamada, R., Determination of N-methyl-D-aspartate in tissues of bivalves by high-performance liquid chromatography. J. Chromatogr. B Biomed. Sci. Appl. 728 (1999), 41–47, 10.1016/S0378-4347(99)00089-4.
Kato, S., Masuda, Y., Konishi, M., Oikawa, T., Enantioselective analysis of D- and L-amino acids from mouse macrophages using high performance liquid chromatography. J. Pharm. Biomed. Anal. 116 (2015), 101–104, 10.1016/j.jpba.2015.04.028.
Roux, A., Blanchot, G., Baglin, A., Flouvat, B., Liquid chromatographic analysis of propranolol enantiomers in human blood using precolumn derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate. J. Chromatogr. B Biomed. Sci. Appl. 570 (1991), 453–461, 10.1016/0378-4347(91)80553-O.
Rosseel, M.T., Vermeulen, A.M., Belpaire, F.M., Reversed-phase high-performance liquid chromatographic analysis of atenolol enantiomers in plasma after chiral derivatization with (+)-1-(9-fluorenyl)ethyl chloroformate. J. Chromatogr. B Biomed. Sci. Appl. 568 (1991), 239–245, 10.1016/0378-4347(91)80359-K.
Wan, H., Blomberg, L.G., Enantiomeric and diastereomeric separation of di- and tripeptides by capillary electrophoresis. J. Chromatogr. A 758 (1997), 303–311, 10.1016/S0021-9673(96)00726-1.
Kuwada, M., Teramoto, T., Kumagaye, K.Y., Nakajima, K., Watanabe, T., Kawai, T., Kawakami, Y., Niidome, T., Sawada, K., Nishizawa, Y., Katayama, K., Omega-agatoxin-TK containing D-serine at position 46 but not synthetic omega-[L-Ser46]agatoxin-TK, exerts blockade of P-type calcium channels in cerebellar Purkinje neurons. Mol. Pharmacol. 46 (1994), 587–593.
Yasuda, A., Yasuda, Y., Fujita, T., Naya, Y., Characterization of crustacean hyperglycemic hormone from the crayfish (Procambarus clarkii): multiplicity of molecular forms by stereoinversion and diverse functions. Gen. Comp. Endocrinol. 95 (1994), 387–398, 10.1006/gcen.1994.1138.
Tarui, A., Shibata, K., Takahashi, S., Kera, Y., Munegumi, T., Yamada, R.-H., N-Methyl-D-glutamate and N-methyl-L-glutamate in Scapharca broughtonii (Mollusca) and other invertebrates. Comp. Biochem. Physiol. Part B Biochem. Mol. Biol. 134 (2003), 79–87, 10.1016/S1096-4959(02)00231-2.
Fujimori, T., Abe, H., Physiological roles of free D- and L-alanine in the crayfish Procambarus clarkii with special reference to osmotic and anoxic stress responses. Comp. Biochem. Physiol. Part A Mol. Integr. Physiol. 131 (2002), 893–900, 10.1016/S1095-6433(02)00006-5.
Gogami, Y., Okada, K., Oikawa, T., High-performance liquid chromatography analysis of naturally occurring D-amino acids in sake. J. Chromatogr. B 879 (2011), 3259–3267, 10.1016/j.jchromb.2011.04.006.
Iwakoshi, E., Hisada, M., Minakata, H., Cardioactive peptides isolated from the brain of a Japanese octopus, Octopus minor. Peptides 21 (2000), 623–630, 10.1016/S0196-9781(00)00201-1.
Hayashi, T., Sasagawa, T., A method for identifying the carboxy terminal amino acid of a protein. Anal. Biochem. 209 (1993), 163–168, 10.1006/abio.1993.1097.
Errico, F., Mothet, J.P., Usiello, A., D-Aspartate. An endogenous NMDA receptor agonist enriched in the developing brain with potential involvement in schizophrenia. J. Pharm. Biomed. Anal. 116 (2014), 7–17, 10.1016/j.jpba.2015.03.024.
Samakashvili, S., Ibáñez, C., Simó, C., Gil-Bea, F.J., Winblad, B., Cedazo-Mínguez, A., Cifuentes, A., Analysis of chiral amino acids in cerebrospinal fluid samples linked to different stages of Alzheimer disease. Electrophoresis 32 (2011), 2757–2764, 10.1002/elps.201100139.
Benedetti, M.S., Frigerio, E., Tocchetti, P., Brianceschi, G., Castelli, M.G., Pellizzoni, C., Dostert, P., Stereoselective and species-dependent kinetics of reboxetine in mouse and rat. Chirality 7 (1995), 285–289, 10.1002/chir.530070416.
Gunaratna, C., Kissinger, P.T., Investigation of stereoselective metabolism of amphetamine in rat liver microsomes by microdialysis and liquid chromatography with precolumn chiral derivatization. J. Chromatogr. A 828 (1998), 95–103, 10.1016/S0021-9673(98)00822-X.
Aturki, Z., Vichi, F., Messina, A., Sinibaldi, M., Indirect resolution of ß-blocker agents by reversed-phase capillary electrochromatography. Electrophoresis 25 (2004), 607–614, 10.1002/elps.200305691.
Tóth, G.K., Bakos, K., Penke, B., Pávó, I., Varga, C., Török, G., Péter, A., Fülöp, F., Synthesis of oxytocin antagonists containing conformationally constrained amino acids in position 2. Bioorg. Med. Chem. Lett. 9 (1999), 667–672, 10.1016/S0960-894X(99)00041-4.
Péter, A., Vékes, E., Török, G., Application of(S)-N-(4-nitrophenoxycarbonyl) phenylalanine methoxyethyl ester as a new chiral derivatizing agent for proteinogenic amino acid analysis by high-performance liquid chromatography. Chromatographia 52 (2000), 821–826, 10.1007/BF02491012.
Itoh, E., Nishida, Y., Togashi, Y., Ohrui, H., Meguro, H., Simultaneous analysis of enantiomeric amino acids based on derivatization with (S)-(+)-2-t-Butyl-2-methyl-1, 3-benzodioxole-4-carboxylic acid and high-Performance liquid chromatography. Anal. Sci. 12 (1996), 551–556, 10.2116/analsci.12.551.
Meguro, H., Ohrui, H., Strategy and design of novel reagents for the fluorometric analysis of biomolecules. Biosci. Biotechnol. Biochem. 60 (1996), 1919–1924, 10.1271/bbb.60.1919.
Meguro, H., Kim, J.-H., Bai, C., Nishida, Y., Ohrui, H., Some applications of a chiral fluorometric reagent, (S)-TBMB carboxylic acid. Chirality 13 (2001), 441–445, 10.1002/chir.1059.
Nishida, Y., Itoh, E., Abe, M., Ohrui, H., Meguro, H., Syntheses of a series of fluorescent carboxylic acids with a 1,3-benzodioxole skeleton and their evaluation as chiral derivatizing reagents. Anal. Sci. 11 (1995), 213–220, 10.2116/analsci.11.213.
Thorsén, G., Engström, A., Josefsson, B., Enantiomeric determination of amino compounds with high sensitivity using the chiral reagents (+)- and (−)-1-(9-anthryl)-2-propyl chloroformate. J. Chromatogr. A 786 (1997), 347–354, 10.1016/S0021-9673(97)00599-2.
Nishi, H., Fukuyama, T., Matsuo, M., Resolution of optical isomers of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (GITC)-derivatized DL-amino acids by micellar electrokinetic chromatography. J. Microcolumn Sep. 2 (1990), 234–240, 10.1002/mcs.1220020506.
Bringmann, G., Lang, G., Steffens, S., Schaumann, K., A. petrosifungins a and B, novel cyclodepsipeptides from a sponge-Derived strain of penicillium b revicompactum §. J. Nat. Prod. 67 (2004), 311–315, 10.1021/np034015x.
Tran, A.D., Blanc, T., Leoplod, E.J., Free solution capillary electrophoresis and micellar electrokinetic resolution of amino acid enantiomers and peptide isomers with L- and D-Marfey's reagents. J. Chromatogr. A. 516 (1990), 241–249, 10.1016/S0021-9673(01)90222-5.
Kleidernigg, O.P., Lindner, W., Indirect separation of chiral proteinogenic (-amino acids using the fluorescence active (1R, 2R)-N-[(2-isothiocyanato)cyclohexyl]-6-methoxy-4-quinolinylamide) as chiral derivatizing agent. J. Chromatogr. A 795 (1998), 251–261, 10.1016/S0021-9673(97)00869-8.
Jin, D., Nagakura, K., Murofushi, S., Miyahara, T., Toyo'oka, T., Total resolution of 17 dl-amino acids labelled with a fluorescent chiral reagent, R(−)-4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole, by high-performance liquid chromatography. J. Chromatogr. A 822 (1998), 215–224, 10.1016/s0021-9673(98)00617-7.
Péter, M., Péter, A., Fülöp, F., Application of (1S, 2S)- and (1R, 2R)-1, 3-diacetoxy-1-(4-nitrophenyl)-2-propylisothiocyanate to the indirect enantioseparation of racemic proteinogenic amino acids. J. Chromatogr. A 871 (2000), 115–126, 10.1016/S0021-9673(99)01090-0.
Fujii, K., Ikai, Y., Mayumi, T., Oka, H., Suzuki, M., Harada, K., A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: elucidation of limitations of marfey's method and of its separation mechanism. Anal. Chem. 69 (1997), 3346–3352, 10.1021/ac9701795.
Brückner, H., Wachsmann, M., Design of chiral monochloro-s-triazine reagents for the liquid chromatographic separation of amino acid enantiomers. J. Chromatogr. A 998 (2003), 73–82, 10.1016/S0021-9673(03)00638-1.
Zhao, M., Bada, J.L., Determination of α-dialkylamino acids and their enantiomers in geological samples by high-performance liquid chromatography after derivatization with a chiral adduct of o-phthaldialdehyde. J. Chromatogr. A. 690 (1995), 55–63, 10.1016/0021-9673(94)00927-2.
Brückner, H., Langer, M., Lüpke, M., Westhauser, T., Godel, H., Liquid chromatographic determination of amino acid enantiomers by derivatization with o-phthaldialdehyde and chiral thiols. Applications with reference to food science, J. Chromatogr. A 697 (1995), 229–245, 10.1016/0021-9673(94)01052-G.
Brückner, H., Westhauser, T., Godel, H., Liquid chromatographic determination of d- and l-amino acids by derivatization with o-phthaldialdehyde and N-isobutyryl-l-cysteine. Applications with reference to the analysis of peptidic antibiotics, toxins, drugs and pharmaceutically used amino acids. J. Chromatogr. A 711 (1995), 201–215, 10.1016/0021-9673(95)00158-j.