Abstract
An up-to-date overview of thin-layer chromatography (TLC) techniques for chiral separations of various significant and/or recent examples of enantioresolutions is reported. Furthermore, examples for chiral separations obtained on achiral commercially available C18 TLC plates are described in detail. These include the enantioseparation of methylthiohydantoin-phenylalanine and methylthiohydantoin-tyrosine using hydroxyethyl-β-cyclodextrin as mobile phase additive and the separation of the enantiomers of warfarin and p-chlorowarfarin using bovine serum albumin as mobile phase additive.
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References
Kowalska T, Sherma J (eds) (2007) Thin layer chromatography in chiral separations and analysis. CRC, Boca Raton, FL
Yuasa S, Shimada A, Kameyama K, Yasui M, Adzuma K (1980) Cellulose thin layer and column chromatography for resolution of DL-tryptophan. J Chromatogr Sci 18:311–314
Contractor SF, Wragg J (1965) Resolution of the optical isomers of dl-tryptophan, 5-hydroxy-dl-tryptophan and 6-hydroxy-dl-tryptophan by paper and thin-layer chromatography. Nature 208:71–72
Haworth DT, Hung Y-W (1973) Thin-layer chromatography of an optically active complex. J Chromatogr 75:314–315
Bach K, Haas HJ (1977) Thin-layer chromatographic separation of racemates of some amino acids. J Chromatogr 136:186–188
Yuasa S, Shimada A, Isoyama M, Fukuhara T, Itoh M (1986) Cellulose conformation responsible for resolution of DL-amino acids. Chromatographia 21:79–82
Wang K (1986) The thin-layer chromatographic separation of enantiomeric dipeptides. Fresenius Z Anal Chem 324:339–340
Kuhn AO, Lederer M, Sinibaldi M (1989) Adsorption chromatography on cellulose. IV. Separation of D- and L-tryptophan and D- and L-methyltryptophan on cellulose with aqueous solvents. J Chromatogr 469:253–260
Lederer M (1992) Adsorption chromatography on cellulose. VII. Chiral separations on cellulose with aqueous solvents. J Chromatogr 604:55–62
Xuan HTK, Kuhn AO, Lederer M (1993) Adsorption chromatography on cellulose VIII. The salting-out behavior of some peptides with aromatic groups. J Chromatogr 626:301–304
Xuan HTK, Lederer M (1993) Adsorption chromatography on cellulose IX. Chiral separations with aqueous solvents and liquid-liquid systems. J Chromatogr 635:346–348
Xuan HTK, Lederer M (1993) Adsorption chromatography on cellulose. X. Adsorption of tryptophan and derivatives from copper sulfate-containing eluents. J Chromatogr 645:185–188
Xuan HTK, Lederer M (1994) Adsorption chromatography on cellulose. XI. Chiral separations with aqueous solutions of cyclodextrins as eluents. J Chromatogr 659:191–197
Chimiak A, Polonsky T (1975) Thin-layer chromatographic separation of diaminodicarboxylic acid stereoisomers and their dansyl derivatives. J Chromatogr 115:635–638
Lederer M (1990) Adsorption chromatography on cellulose. VI. Further studies on the separation of D- and L-tryptophan on cellulose with aqueous solvents. J Chromatogr 510:367–371
Faupel M (1987) A new microcristalline triacetylcellulose thin-layer plate permitting separation of enantiomers. In: Proc. Fourth Int. Symp Instrumental HPTLC, Selvino, Italy
Lepri L, Coas V, Desideri PG, Zocchi A (1994) Reversed phase planar chromatography of enantiomeric compounds on triacetylcellulose. J Planar Chromatogr 7:376–381
Lepri L, Del Bubba M, Masi F (1997) Reversed phase planar chromatography of enantiomeric compounds on microcrystalline cellulose triacetate (MCTA). J Planar Chromatogr 10:108–113
Lepri L, Boddi L, Del Bubba M, Cincinelli A (2001) Reversed phase planar chromatography of some enantiomeric amino acids and oxazolidinones. Biomed Chromatogr 15:196–201
Lepri L (1995) Reversed phase planar chromatography of enantiomeric compounds on microcrystalline triacetylcellulose. J Planar Chromatogr 8:467–469
Lepri L, Del Bubba M, Coas V, Cincinelli A (1999) Reversed-phase planar chromatography of racemic flavanones. J Liq Chromatogr Relat Technol 22:105–118
Lepri L, Cincinelli A, Del Bubba M (1999) Reversed phase planar chromatography of optical isomers on microcrystalline cellulose triacetate (MCTA). J Planar Chromatogr 12:298–301
Lepri L, Del Bubba M, Cincinelli A, Boddi L (2000) Inclusion planar chromatography of enantiomeric and racemic compounds. J Planar Chromatogr 13:384–387
Lepri L, Cincinelli A, Checchini L, Del Bubba M (2010) Structure and substituent effects on retention and chiral resolution of ketones and alcohols on microcrystalline cellulose triacetate plates. Chromatographia 71:685–694
Lepri L, Del Bubba M, Cincinelli A, Boddi L (2001) Direct resolution of aromatic alcohols by planar chromatography on tribenzoyl cellulose as chiral stationary phase. J Planar Chromatogr 14:134–136
Lepri L, Del Bubba M, Cincinelli A, Bracciali M (2002) Quantitative determination of enantiomeric alcohols by planar chromatography on tribenzoylcellulose. J Planar Chromatogr 15:220–222
Del Bubba M, Cincinelli A, Checchini L, Lepri L (2011) Chiral separations and quantitative analysis of optical isomers on cellulose tribenzoate plates. J Chromatogr A 1218:2737–2744
Suedee R, Heard CM (1997) Direct resolution of propranolol and bupranolol by thin-layer chromatography using cellulose derivatives as stationary phase. Chirality 9:139–144
Kubota T, Yamamoto C, Okamoto Y (2000) Tris(cyclohexylcarbamate)s of cellulose and amylose as potent chiral stationary phase for high-performance liquid chromatography and thin layer chromatography. J Am Chem Soc 122:4056–4059
Kriz D, Kriz CB, Andersson LI, Mosbach K (1994) Thin-layer chromatography based on the molecular imprinting technique. Anal Chem 66:2636–2639
Suedee R, Songkram C, Petmoreekul A, Sangkunakup S, Sankasa S, Kongyarit N (1998) Thin-layer chromatography using synthetic polymers imprinted with quinine as chiral stationary phase. J Planar Chromatogr 11:272–276
Suedee R, Srichana T, Saelim J, Thavornpibulbut T (1999) Chiral determination of various adrenergic drugs by thin-layer chromatography using molecularly imprinted chiral stationary phases prepared with α-agonists. Analyst 124:1003–1009
Suedee R, Songkram C, Petmoreekul A, Sangkunakup S, Sankasa S, Kongyarit N (1999) Direct enantioseparation of adrenergic drugs via thin-layer chromatography using molecularly imprinted polymers. J Pharm Biomed Anal 19:519–527
Suedee R, Srichana T, Saelim J, Thavornpibulbut T (2001) Tin-layer chromatographic separation of chiral drugs on molecularly imprinted chiral stationary phases. J Planar Chromatogr 14:194–198
Aboul-Enein HY, El-Awady MI, Heard CM (2002) Direct enantiomeric resolution of some cardiovascular agents using synthetic polymers imprinted (−)-S-timolol as chiral stationary phase by thin-layer chromatography. Pharmazie 57:169–171
Gunther K, Moeller K (2003) Enantiomer separations. In: Sherma J, Fried B (eds) Handbook of thin-layer chromatography, 3rd edn. Marcel Dekker, New York, pp 471–533
Gunther K, Martens J, Schickedanz M (1984) Thin-layer chromatographic enantiomer separation by using ligand exchange. Angew Chem 96:514–515
Weisenstein S (1984) Resolution of optical isomers by thin-layer chromatography. Tetrahedron Lett 25:985–986
Marchelli R, Virgili R, Armani B, Dossena A (1986) Enantiomeric separations of d, l-Dns-amino acids by one- and two-dimensional thin layer chromatography. J Chromatogr 355:354–357
Sinibaldi M, Messina A, Girelli AM (1988) Separation of dansyl amino acid enantiomers by thin-layer chromatography. Analyst 113:1245–1247
Martens J, Lubben S, Bhushan R (1989) Synthese eines neuen chiralen selektors für die dunn-schichtchromatographische enantiomerentrennung nach dem ligandenaustauschprinzip. Tetrahedron Lett 30:7181–7182
Remelli M, Piazza R, Polidori F (1991) HPTLC separation of aromatic α-amino acid enantiomers on a new histidine-based stationary phase using ligand exchange. Chromatographia 32:278–287
Bhushan R, Reddy GP, Joshi S (1994) TLC resolution of dl-amino acids on impregnated silica gel plates. J Planar Chromatogr 7:126–128
Bhushan R, Martens J, Walbaum S, Joshi S, Parshad V (1997) TLC resolution of enantiomers of amino acids and dansyl derivatives using (1R,3R,5R)-2-azabicyclo[3.3.0]octan-3-carboxylic acid as impregnating reagent. Biomed Chromatogr 11:286–288
Bhushan R, Gupta D (2006) Ligand-exchange TLC resolution of some racemic beta-adrenergic blocking agents. J Planar Chromatogr 19:241–245
Metzger H, Maier R, Sitter C, Stern HO (1984) 2-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-(1S,3S,5S)-2-azabicyclo[3.3.0]octane-3-carboxylic acid (Hoe 498)—a new and high effective angiotensin I converting enzyme inhibitor. Arzneim Forsch Drug Res 34:1402–1406
Sajewicz M, Pietka R, Kowalska T (2004) Chiral separation of S(+)- and R(−)-ibuprofen by thin-layer chromatography. An improve analytical procedure. J Planar Chromatogr 17:173–176
Sajewicz M, Pietka R, Kowalska T (2005) Chiral separation of ibuprofen and propranolol by TLC. A study of the mechanism and thermodynamic of retention. J Liq Chromatogr Relat Technol 28:2499–2513
Paris RR, Sarsunova M, Semonsky M (1967) La Chromatographie en couche mince comme methode de dedoublement des alcalaoides racemiques. Application aux medicaments contenant de l’ephedrine. Ann Pharm Fr 25:177–180
Bhushan R, Martens J, Arora M (2001) Direct resolution of (+)-ephedrine and atropine into their enantiomers by impregnated TL. Biomed Chromatogr 15:151–154
Bhushan R, Ali I (1987) Resolution of enantiomeric mixtures of phenyl-thiohydantoin amino acids on (+)-tartaric acid impregnated silica gel. J Chromatogr 392:460–463
Bhushan R, Ali I (1987) TLC resolution of enantiomeric mixtures of amino acids. Chromatographia 23:141–142
Bhushan R, Thiong’o GT (1999) Direct enantiomeric resolution of some 2-arylpropionic acids using (−)-brucine-impregnated thin-layer chromatography. Biomed Chromatogr 13:276–278
Bhushan R, Gupta D (2004) Resolution of (+)-ibuprofen using (−)-brucine as a chiral selector by thin-layer chromatography. Biomed Chromatogr 18:838–840
Bhushan R, Ali I (1993) Resolution of racemic mixtures of hyoscyamine and colchicine on impregnated silica gel layers. Chromatographia 35:679–680
Bhushan R, Arora M (2003) Direct enantiomeric resolution of (+)-atenolol, (+)-metoprolol and (+)-propranolol by impregnated TLC using L-aspartic acid as chiral selector. Biomed Chromatogr 17:226–230
Bhushan R, Parshad V (1996) Resolution of (+)-ibuprofen using L-arginine-impregnated thin-layer chromatography. J Chromatogr A 721:369–372
Sajewicz M, Pietka R, Dabrik G, Namyslo E, Kowalska T (2006) On the stereochemically peculiar two-dimensional separation of 2-arylpropionic acids by chiral TLC. J Planar Chromatogr 19:273–277
Bhushan R, Thiong’o GT (1998) Direct enantioseparation of some beta-adrenergic blocking agents using impregnated thin-layer chromatography. J Chromatogr B 708:330–334
Bhushan R, Martens J, Thiong’o GT (2000) Direct thin-layer chromatography enantioseparation of some basic DL-amino acids using a pharmaceutical industry waste as chiral impregnating reagent. J Pharm Biomed Anal 21:1143–1147
Aboul-Enein R, El-Awady MI, Heard CH (1998) Enantiomeric resolution of some 2-arylpropacids using L-(−)-serine-impregnated silica as stationary phase by thin-layer chromatography. J Pharm Biomed Anal 32:1055–1059
Bhushan R, Martens J (2001) Separation of amino acids, their derivatives and enantiomers by impregnated LC. Biomed Chromatogr 15:155–165
Bhushan R, Parshad V (1996) Thin-layer chromatographic separation of enantiomeric dansyl amino acids using a macrocyclic antibiotic as a chiral selector. J Chromatogr A 736:235–238
Bhushan R, Thiong’o GT (2000) Separation of the enantiomers of dansyl-DL-amino acids by normal-phase TLC on plates impregnated with a macrocyclic antibiotic. J Planar Chromatogr 13:33–36
Bhushan R, Gupta D (2005) Thin-layer chromatography separation of enantiomers of verapamil using macrocyclic antibiotic as chiral selector. Biomed Chromatogr 19:474–478
Wainer I, Brunner C, Doyle T (1983) Direct resolution of enantiomers via thin-layer chromatography using a chiral adsorbent. J Chromatogr 264:154
Wall PE (1989) Preparation and application of TLC plates for enantiomer separation. Proc Int Symp Instrumental thin-layer chromatography/planar chromatography, Brighton, Sussex, U.K., p 237
Wall PE (1989) Preparation and application of HPTLC plates for enantiomer separation. J Planar Chromatogr 2:228–232
Armstrong DW, He FY, Han SM (1988) Planar chromatographic separation of enantiomers and diastereomers with cyclodextrin mobile phase additives. J Chromatogr 448:345–354
Armstrong DW, Faulkner JR Jr, Han SM (1988) Use of hydroxypropyl- and hydroxyethyl-derivatized beta-cyclodextrins for the thin-layer chromatographic separation of enantiomers and diastereomers. J Chromatogr 452:323–330
Duncan JD, Armstrong DW (1990) Chiral mobile phase additives in reversed-phase TLC. J Planar Chromatogr 3:65–67
LeFevre JW (1993) Reversed-phase thin-layer chromatographic separations of enantiomers of dansyl-amino acids using β-cyclodextrin as a mobile phase additive. J Chromatogr 653:293–302
Lepri L, Coas V, Desideri PG, Checchini L (1990) Separation of optical and structural isomers by planar chromatography with development by β-cyclodextrin solutions. J Planar Chromatogr 3:311–316
Lepri L, Coas V, Desideri PG (1990) Planar chromatography of isomers using β-cyclodextrin solutions as mobile phases. J Planar Chromatogr 3:533–535
Lepri L, Coas V, Desideri PG (1991) Reversed phase planar chromatography of isomers using α-and β-cyclodextrin solutions as eluents. J Planar Chromatogr 4:338–340
Lepri L, Coas V, Desideri PG (1994) Planar chromatography of optical and structural isomers with eluents containing modified β-cyclodextrins. J Planar Chromatogr 7:322–326
Lepri L, Coas V, Desideri PG, Zocchi A (1994) The mechanism of retention of enantiomeric solutes on silanized silica plates eluted with albumin solutions. J Planar Chromatogr 7:103–107
Lepri L, Coas V, Desideri PG (1992) Planar chromatography of optical isomers with bovine serum albumin in the mobile phase. J Planar Chromatogr 5:175–178
Lepri L, Coas V, Desideri PG, Zocchi A (1992) Reversed phase planar chromatography of enantiomeric tryptophans with bovine serum albumin in the mobile phase. J Planar Chromatogr 5:234–238
Lepri L, Coas V, Desideri PG (1992) Reversed phase planar chromatography of optically active fluorenylmethoxycarbonyl amino acids with bovine serum albumin in the mobile phase. J Planar Chromatogr 5:294–296
Lepri L, Coas V, Desideri PG, Pettini L, Santianni D (1992) Reversed phase planar chromatography of enantiomeric compounds with bovine serum albumin in the mobile phase. J Planar Chromatogr 5:364–367
Lepri L, Coas V, Desideri PG, Santianni D (1993) Reversed-phase planar chromatography of dansyl DL amino acids with bovine serum albumin in the mobile phase. Chromatographia 36:297–301
Lepri L, Coas V, Desideri PG, Pettini L (1993) Thin-layer chromatographic enantioseparation of miscellaneous compounds with bovine serum albumin in the eluent. J Planar Chromatogr 6:100–104
Lepri L, Coas V, Del Bubba M, Cincinelli A (1999) Reversed-phase planar chromatography of optical isomers with bovine serum albumin as mobile-phase additive. J Planar Chromatogr 12:221–224
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Del Bubba, M., Checchini, L., Cincinelli, A., Lepri, L. (2013). Enantioseparations by Thin-Layer Chromatography. In: Scriba, G. (eds) Chiral Separations. Methods in Molecular Biology, vol 970. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-263-6_2
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DOI: https://doi.org/10.1007/978-1-62703-263-6_2
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