Anal. Chem.

2006, 78, 3947

Chiral Separations
Timothy J. Ward*

Millsaps College, 1701 North State Street, Box 150306, Jackson, Mississippi 3921
Review Contents Reviews Capillary Electrophoresis (CE) High-Performance Liquid Chromatography (HPLC) Gas Chromatography (GC) Supercritical Fluid Chromatography (SFC) Thin-Layer Chromatography (TLC) Capillary Electrochromatography (CEC) Multiple Technique Reviews Capillary Electrophoresis Cyclodextrins Antibiotics Micelles Microchip CE Miscellaneous Thin-Layer Chromatography Supercritical Fluid Chromatography and Related Techniques Gas Chromatography Applications and Mechanistic Studies Novel CSPs High-Performance Liquid Chromatography Polysaccharide CSPs Macrocyclic Antibiotic CSPs Cyclodextrin CSPs and Mobile-Phase Additives Protein-Based CSPs Miscellaneous CSPs Capillary Electrochromatography Miscellaneous Techniques Literature Cited 3947 3947 3947 3947 3947 3948 3948 3948 3948 3948 3949 3949 3949 3949 3949 3949 3950 3950 3950 3950 3950 3951 3951 3952 3952 3952 3953 3953

covering chiral separations are presented first, followed by an examination of the methods and techniques utilized in each area. REVIEWS Capillary Electrophoresis (CE). Capillary electrophoresis remains a popular technique for the enantioseparation of biologically active compounds. Enantiomeric separations by CE employing nonaqueous conditions were reviewed by Laemmerhofer (2), with the focus on solvent effects on chiral recognition and separation mechanism. Riekkola and Siren (3) also reviewed enantioseparations by CE in nonaqueous media. The use of macrocyclic glycopeptides as chiral selectors in CE was reviewed (4), and procedures for their use were described. A review of CE in the chiral separation of nonsteroidal antiinflammatory drugs was presented by Patel et al. (5) with applications including the detection of enantiomeric composition after synthesis, chiral impurity profiles in bulk drugs and formulated products, and metabolite profiles in biological fluids. The chiral analysis of pollutants and their metabolites by CE was reviewed by Hernandez-Borges et al. (6), with emphasis on articles published in the last 10 years. Recent advances in the analysis of small achiral and chiral solutes by CE-mass spectrometry were discussed by Shamsi and Miller (7), with application areas including pharmaceuticals, agrochemicals, carbohydrates, and small peptides. (Additional reviews of chiral separations are listed in Multiple Techniques Reviews.) High-Performance Liquid Chromatography (HPLC). An overview of enantiomeric separations by HPLC using macrocyclic glycopeptide-based chiral stationary phases (CSPs) was discussed by Xiao and Armstrong (8), including materials, methods, and notes. Roussel et al. (9) reviewed examples in which chiral HPLC was combined with classical methods such as NMR or CD for the on- or off-line detection of the absolute configuration of enantiomers. A review of penicillin G acylase-based CSPs was compiled by Calleri et al. (10), focusing on immobilization methods, materials, and applications in chiral HPLC. An exhaustive compilation of the separation of agrochemical enantiomers by HPLC on commercial CSPs was given by Felix (11). Gas Chromatography (GC). A review of original research papers from 2001 to 2005 dealing with the applications of chiral GC for direct enantioseparation of optically active compounds was presented (12), with applications grouped by CSP types and fields of interest, including natural products, asymmetric synthesis, environmental contaminants, and compounds important to space science, agricultural, food, flavor, and fragrance industries. Supercritical Fluid Chromatography (SFC). The use of SFC for the rapid screening and optimization approach for enantioseparations of pharmaceuticals was discussed (13), with a success rate of over 95% for an automated system. The analytical scale
Analytical Chemistry, Vol. 78, No. 12, June 15, 2006 3947

This fundamental review article covers developments and applications in chiral separations from January 2004 to January 2006 and is restricted to the English language literature. If the numbers of publications appearing during the last several review periods are used as a guide for the acceptance of a technique, it is clear that chiral HPLC is a well-established and widely accepted tool in the analytical laboratory. It is interesting to note that approximately 20 years ago, in a 1987 A-pages review article, Armstrong (1) observed that, “...we are not far from the point when the majority of enantiomeric separations will be considered routine.” While the technique clearly has become a well-used tool in the laboratory, it is not far from becoming a classical technique and one that still generates significant interest in the scientific literature. With the tremendous number of publications in this field, a comprehensive review of all published papers is not feasible, and thus, this fundamental review focuses on major developments and trends in the field of chiral separations, as well as representative applications. Several excellent general reviews
* Phone: (601) 974-1405. Fax: (601) 974-1401. E-mail: wardtj@millsaps.edu. 10.1021/ac060622o CCC: $33.50 Published on Web 00/00/0000 © 2006 American Chemical Society

Cyclodextrins. 2006 . (24). Where possible. A review of the use of molecularly imprinted polymers (MIPs) for chiral drug separations in HPLC. A screening strategy for the development of enantiomeric separation methods in capillary electrophoresis was developed by Jimidar et al. (15). HPLC. The antidepressant mirtazapine and its active demethylated metabolite were enantioseparated by CE using carboxymethyl-βCD as chiral selector (30). Thin-Layer Chromatography (TLC). CEC. Novel CSPs for GC and LC were developed and discussed by Oi (25). micellar electrokinetic chromatography (MEKC). The achievements in chiral separations by TLC from 2001 to 2005 were reviewed by Siouffi et al. β-CD was used as chiral selector in the CE separation of dopamino-derived neurotoxins (36) and the enantioseparation of simendan enantiomers (37). The chiral selector 2. and an elution order reversal was noted when β-CD was added to the system (56). This is no doubt due to their solubility and stability in aqueous solution. The chiral separation of anticholinergic drug enantiomers by nonaqueous CE was achieved using heptakis(2. Sulfated β-CDs were characterized and used in the determination of enantiomeric purity of (1R. and rod-CEC. with emphasis on cellulose derivatives and especially microcrystallized cellulose triacetate. TLC. and separation mechanisms of TLC enantiomeric separations was discussed by Guenther et al. Basic compounds were enantioseparated using heptakis(2. 78. Multiple Technique Reviews.1′-binaphthyl-2. including open tubular CEC. and the enantioseparation of hydrobenzoin and related compounds by CZE (42). The use of electrodriven methods including CE. A mixture of sulfobutyl ether-β-CD and dimethyl-β-CD was used as chiral selectors in the validated CE method for the chiral purity of ragaglitazar (58) and the enantioseparation of glitazone compounds (59). (17).2′-diyl hydrogen phosphate as a test solute. and a preparative-scale enantioseparation by GC was presented. and CEC was compiled by Ansell (20). as well as screening techniques and method optimizations. CEC. and weak base analytes (49-51) Cyclodextrins were chiral selectors used in the chiral analysis of ephidrine (52) and adrenergic amines (53) in dietary supplements.3-di-O-ethyl6-O-sulfo)-β-CD was used as chiral selector for the determination of salbutamol enantiomers by nonaqueous CE (55). A review of chiral separations by CEC using cyclodextrin CSPs was given by Wistuba et al. and the influence of methanol was studied on the enantioresolution of antihistamines again employing carboxymethyl-β-CD as chiral selector (33).chiral separations were also adapted for semipreparative work. SFC. Sulfated R-CDs were synthesized.3dihydroxy-6-O-sulfo)-β-CD was used in the CZE enantioseparation of hydrobenzoin. tramadol enantiomers and metabolites (46). applicability. with an overview of direct and indirect separations. SFC. A study on the reproducibility of CE enantioresolution with randomly substituted cyclodextrins was reported (29). A review focusing on the advances in CSPs in chiral separations of drugs in HPLC and SFC was discussed by Zhang et al. (27). Succinyl-β-CD was used as chiral selector in the determination of phenylglycidol enantiomers by CE (35). Chiral separations by CEC in nonaqueous media were reviewed by Laemmerhofer (16) The chiral selectors and columns used in highly efficient enantioseparations are thoroughly described. (28). N-imidazole derivatives (44).2S)-ephedrine by CZE (41). with cyclodextrin (CD) use as chiral selectors remaining high. and carboxylmethyl-β-CD showed the 3948 highest chiral separation power as chiral selector for the enantiomeric separation of the sunscreen agent 3-(4-methylbenzylidene)camphor by EKC (31). and heptakis(2. Chiral separations in HPLC and CE were reviewed (22). Vol. The use of Marfey’s reagent for preparing CSPs for direct enantiomeric resolution was described by Bhushan and Brueckner (26). Chiral selectors are also discussed. Heptakis(2. The sulfated β-CDs were also used for the enantioresolution of baclofen (43). Carboxymethyl-β-CD was found to give outstanding enantioresolution of deprenyl-N-oxide isomers by CE (34).3di-O-methyl-6-O-sulfo)-β-CD in combination with potassium camphorsulfonate in nonaqueous CE (54). The analysis of chiral pollutants using GC. Hydroxypropyl-R-CD and hydroxypropyl-β-CD were found to give good results in the capillary zone electrophoresis (CZE) enantioseparation of N-imidazole derivatives (39). and new nucleoside analogues related to d4T and acyclovir (47). The addition of methanol was found to enhance the enantioseparation of dimetindene using carboxymethyl-β-CD as chiral selector in CE (32). The enantioseparation of a mixture of seven carboxybenzylamino acids was achieved by heptakis(6-amino-6-deoxy)-β-CD by CE (62). The influence of (hydroxy)alkylamino substituents on the enantioresolution abililty of singleisomer amino-β-CD derivatives in chiral CE was reported (61). and TLC was discussed by Aboul-Enein and Ali (18). packed CEC. non-UV-absorbing properties. An overview of the versatility. cost. data were compared to that obtained by HPLC. using 1.3-dimethyl-6-sulfato)-β-CD (57). CAPILLARY ELECTROPHORESIS Methods and research in CE continues to be a major area of chiral analytical separations. and used as the chiral selector for the CE enantioseparation of nonionic. and tryptophan was demonstrated using two additives: sulfated-β-CD as the chiral selector and dextran sulfate (48). weak acid. characterized. By far the most popular chiral selector used in CE remains the cyclodextrins. A positively charged quaternary ammonium β-CD derivative was used as the chiral selector in the CE separation of highly negatively charged enantiomers (60). Capillary Electrochromatography (CEC). The theory and practice of enantioselective capillary chromatography using metal coordination compounds and modified cyclodextrins as CSPs are discussed by Schurig (23). rivastigmine in pharmaceuticals (45). tyrosine. 12. and MEKC for the enantioseparation of second-generation antidepression drugs was reviewed by Mandrioli and Raggi (19). (14). Control of enantioselectivity of the separation of enantiomers of phenylalanine. No. Mono(6-amino-6-deoxy)-β-CD was used as chiral selector in Analytical Chemistry. with another review of MIPs in chiral HPLC and CE written by Turiel and Martin-Esteban (21). June 15.6-dimethyl-βCD was used in the enantioresolution of calcium levofolinate (38). and excellent selectivity offered through the various cyclodextrin derivatives. A discussion and commentary on the feasibility of the separation of enantiomers by CE based solely on equal binding constants between analyte enantiomers and the chiral selector was given by Chankvetadze et al. The enantioseparation of derivatized serine by CE was accomplished using hydropropylβ-CD (40).

Subsecond chiral separations on a microchip using highly sulfated γ-CD as chiral selectors to separate DNS-amino acids (84) achieved a baseline separation in 720 ms. (81). with the first reported attempt of a computer simulation of the CD-SDS-MCE system. The enantioseparation of chiral allenic acids by MEKC using CDs as chiral selectors has been described (76).and (R)levetiracetam (77). and a TLC method for the enantioseparation of ibuprofen was used in physicochemical studies of the oscillatory instability of profens when stored for long periods in aqueous media (95). The role of the sugar moiety of glycopeptide antibiotics in chiral recognition was investigated with CE using vancomycin and balhimycin as models (69). nadolol. and the applicability to quality control of pharmaceuticals was discussed. A method using silica gel plates and (-)-brucine as a chiral selector was reported for the enantioseparation of ibuprofen (97). Enantioseparation of furan derivatives and fused polycycles were performed using CDmodified MCE (72). No. acidic rac-2-phenylpropionic acid.5-dinitrobenzoyl leucine (91). The effect of oil substitution in chiral MEEKC was studied (79). The chiral separation of labetalol in human plasma was achieved using a new γ-CD derivative as the chiral selector (68). An affinity CE method using human serum albumin as chiral selector was employed in the enantioseparation of propranolol (87).and L-tryptophan. and robustness studies for racemic citalopram (67). Chiral CE using (+)-18crown-6-tetracarboxylic acid was employed in the complete enantioseparations of eight aromatic amino acids and four alkyl esters of 2-phenylglycine (86). An effective method to form a protein CSP for fast enantioseparation with electrochemical detection on a microchip was presented by Bi et al. 2006 3949 . Miscellaneous. Micelles. Antibiotics. The chiral separation of amino acid derivatives by ligand-exchange electrophoresis in a microchannel chip was performed using a Cu(II) complex with L-prolinamide as chiral selector (83). The effect of several experimental parameters in micellar capillary electrophoresis (MCE) was studied using a system of SDS and hydroxypropyl-β-CD as the chiral selector (71) as the model. and mono-6A-butylammonium-6A-deoxy-β-CD tosylate was investigated for the enantioseparation of R-hydroxy acids. The Kromasil CHI-TBB column was used in an isocratic subcritical/SFC method for the separation of naproxen enantiomers (101). A 3-amino derivative of β-CD and its Cu(II) complexes were studied as a chiral ligand exchanger for the enantioseparation of tyrosine and phenylalanine (65). A reversible gel based on guanosine was introduced as chiral selector in CE (92). Cationic vesicles were used as chiral selector for the MEKC enantioseparation of nonsteroidal antiinflammatory drugs (75). isoproterenol. and prediction of enantiomer migration orders by a three-dimensional quantitative structure-property relationship/comparative field analysis model was performed. The TLC enantioseparation of verapamil was achieved using the macrocyclic antibiotic vancomycin as the chiral selector impregnated on silica gel plates (98). Balhimycin and its halo analogue bromobalthimycin were thoroughly evaluated as chiral selectors for enantioresolution by CE (70). 94). The solutes norephedrine. and the enantioseparation of propranolol was achieved. and basic rac-1-phenylethylamine was achieved using subcritical and SFC with two different CSPs. ephedrine. it remains a reliable separation technique.S)-3. neutral rac-R-tetralol. Capillary zone electrophoresis using (+)-18crown-6-tetracarbonic acid and CD as chiral selectors was used to enantioseparate amino acids and some amino acid derivatives including esters and dipeptides (85). and carboxymethyl-γ-CD chiral selector was also used in the CE enantiomeric determination. Chiral separations of ibuprofen and propranolol were reported on commercially available TLC plates with detection by densitometry (93. Sulfated cyclosophoraoses were synthesized and used as novel chiral selectors for the CE enantioseparation of five β-blockers: arterenol. A nonaqueous CE method using O-(tert-butylcarbamoyl)quinine as chiral selector and detection by FT-IR was used to separate the enantiomers of (R. carboxylic acids.the enantiomeric separation of a variety of anionic analytes (63). Human serum albumin was also used as chiral selector in the CE partial-filling method to resolve bupivacaine enantiomers (88). SUPERCRITICAL FLUID CHROMATOGRAPHY AND RELATED TECHNIQUES Supercritical fluid chromatography and related techniques were employed in the separation of various racemates using a variety of CSPs. The use of CD modified microemulsion electrokinetic chromatography (MEEKC) was applied to enantioresolve (S). Cu(II)-prolinamides were used as chiral selector in a ligandexchange CE method for the chiral resolution of dansyl amino acids (89). and propranolol were enantioresolved by a MEEKC method using chiral alcohols as cosurfactants (80). Vol. atenolol. SFC and HPLC were used in the enantioseparation of carbobenzyloxy derivatives of amines (99). The enantioseparation of anisodamine by CE using carboxymethyl-γ-CD as chiral selector was validated (66). The enantiomeric separation of hydrophobic dihydrofuroflavones were performed using hydroxypropyl-γ-CD by micellar CE (73). and ampholytic analytes (64). (74). and the effect of surfactant concentration and buffer selection was discussed. using BSA as the protein and enantioresolving D. THIN-LAYER CHROMATOGRAPHY Though TLC is used less often than other separation techniques in enantioresolution methods. (96). A reversal of elution order for some 2-substituted propionic acid drugs was observed in SFC on Chiralpak AD when the polar modifier methanol in carbon dioxide was replaced by 2-propanol (102). June 15. The direct separation of the enantiomers of metoprolol tartrate employing the chiral mobile-phase additive D-(-)-tartaric acid on impregnated TLC plates was reported by Lucic et al. 78. validation. A combination of cyclodextrins and polymeric surfactants was investigated for chiral separation of three binaphthyl derivatives in MEKC by Warner et al. MEEKC with the chiral surfactant dodecoxycarbonylvaline was used in the investigation of the enantioseparation of 15 different pharmaceutical compounds (78). 12. Separation of the enantiomers of three different racemates. Microchip CE. using polysaccharide and Pirkle-type CSPs. with the most effective chiral selector found to be γ-CD. propranolol. A Chiralcel OD column was used in the SFC Analytical Chemistry. The chiral separation of gemifloxacin using (+)-18-crown-6-tetracarboxylic acid as a chiral selector was performed by microchip electrophoresis (82). Sumichiral OA-7500 (a derivatized β-cyclodextrin) and Chiralpak AD-H (a derivatized amylose) (100). and metoprolol (90).

The major ibuprofen metabolites in human urine were enantioresolved by a Chiralpak AS column (134).3-di-O-methyl-6-O-tert-butyldimethylsilyl)-β-CD as the CSP (113). epoxides. 3950 and 2. The chiral HPLC analysis of naringenin was achieved on a Chiralcel OD-RH CSP and was successfully applied to analysis of rat and human urine (137). and OB.3-di-O-methyl-6-O-tertbutyldimethylsilyl)-β-CD as a CSP was reported by Shitangkoon et al. propargyllone acetate. A key intermediate of zolmitriptan in bulk drugs was enantioseparated by Chiralpak AD-H CSP in a validated method (133). and a Chiralpak AD-RH column was used in the chiral analysis of ibuprofen in urine (135). and human adipose tissues was achieved using a modified CD as CSP (111). The effect of the Chiralpak AD CSP structural change with mobile-phase modifier on the chiral selectivity was investigated (130). OJ. sulfoxides. A set of racemic acidic drugs were enantioseparated on an immobilized Chiralpak IA column and coated Chiralpak AD column. Applications and Mechanistic Studies. fenoprofen. and mechanistic aspects were reported. Chiralcel OD and Chiralpak AS columns were found to be excellent for direct enantioseparation of the fungicide ethaboxam (132). and Chirobiotic V.6-dimethyl-3-pentyl β. A new class of CD derivatives based on 2. exhibiting significant impact on the chiral selectivity of the amino acid esters. The HPLC enantioseparation of naringenin and other flavanones was accomplished using Chiralcel OD-H and Chiralpak AS-H columns using various hexane/alcohol mobile phases (138). The enantiomers of chiral epoxides were resolved on CSPs of four new CD derivatives: 2. and ketoprofen methyl esters mixture used heptakis-(2. 2. Chiral GC analysis of cyclopropane derivatives was attained with a baseline separation using a Chirasil-β-dex CSP (110). including allethrone acetate. and γ-cyclodextrin stationary phases was studied (107). the polysilane and cyclodextrin pseudophase. The enantiomeric separation of methylsulfonyl PCB metabolites in seal blubber. and the separations were compared (136). Novel CSPs. A SFC method using a Chiralpak AD column for the enantiomeric separation of a peroxysome proliferator-activating receptor agonist drug was developed. June 15. A thermodynamic study on the GC enantioseparation of aromatic alcohols using heptakis(2.and γ-CD stationary phases (108). (119). The first enantiomeric separations using chiral ionic liquids as stationary phases in GC were reported by Armstrong et al. With many CSPs available from using in chiral HPLC. The use of preparative chiral HPLC in a preclinical drug discovery strategy was described (127).6-diO-benzyl-3-O-octanonyl-β-CD.6-di-O-benzyl-3-O-heptanonyl-β-CD. GAS CHROMATOGRAPHY Chiral resolutions by GC continued to find strong application in various fields.3-di-O-methoxymethyl-6tert-butyldimethylsilyl-γ-CD were reported to be suitable for the enantioresolution of a broad spectrum of chiral volatiles from different chemical classes (124). The theory and use of the three-phase model in enantioselective gas-liquid chromatography using a methylated CD/polysiloxane stationary phase was presented (106). The enantiomeric ratio of 1-octen-3-ol in various species of edible mushrooms was investigated using chiral GC (116). 2006 . and acetylated amines. (126). were investigated as CSPs for the separation of racemic N-trifluoroacetyl-O-alkyl esters of R-amino acids (122). Four CD derivatives with allyl groups or propyl groups on the 3-position of β-CD were synthesized and used as CSPs for capillary GC for the enantioseparation of various racemates. and 2-bromopropionic acid methyl ester (121). BGB-172 (118). the most popular CSPs used during this review period were the polysaccharide CSPs and not surprisingly they also had the largest increase in the number of applications reported. and T.3-di-O-benzyl-6-O-heptanonyl-β-CD. 2. and equations derived that accounted for all three partition equilibria for the analyte in the system. No. The determination of the enantiomeric excess of (+)-chlorofluoroiodomethane was obtained from GC using a chiral modified CD CSP (115). OF. diols. with unusually high separation factors for 2-alkyl esters of short-chain (C2-C6) acids (123).separation of the enantiomers of 1-phenyl-1-propanol (103).3-di-O-benzyl-6-O-octanonyl-β-CD (120). An optimized chiral GC method for the enantioseparation of ibuprofen. and several novel CSPs were reported. A validated chiral HPLC method for the separation of mebeverine enantiomers was reported using a Chiralcel OD column (131). A GC/ MS method using a chiral capillary column was reported for the separation of the enantiomers of ibuprofen from tablets (112). Strategies for method development of chiral separations in normal. The separation of the enantiomers of N-TFA-O-alkyl amino acids on 2.or reversed-phase liquid chromatography using polysaccharide-based stationary phases were reported by Matthijs et al. β-. The enantiomers of the synthetic pyrethroid insecticides cypermethrin and cyfluthrin were separated by a β-CD-based CSP. The effect of the addition of (+) or (-) camphorsulfonic acid to the mobile phase was investigated on the enantioseparations of some basic drugs on a Chiralcel OD column (128). 78. including partitioning between the gas mobile phase and both stationary-phase components. pelican muscle. Three peralkylated β-cyclodextrins were coated onto a fused-silica capillary by the sol-gel method and exhibited thermal stability and enantioselectivity (125). Chiralcel OD. with the enantiomeric purity determined within 10 min on a 5-cm column (104).3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl)-βCD was found to be suitable for the enantioseparation of volatiles from various chemical classes. Eight 2-substituted ethyl propionate enantiomers were enantioseparated on permethylated and 2. 12. (109). A SFC-tandem mass spectrometry method using a Chiralcel OD-H column was developed for the enantioselective detection of propranolol and pindolol in mouse blood by serial sampling (105).3-di-O-pentyl6-O-acyl R-. Modified linear dextrins. dubbed acylclodextrins. with separated compounds including alcohols. The CSP based on heptakis(2. Chiral PCBs in food samples were enantioseparated on commercially available chiral capillary β-CD columns by means of heart-cut multidimensional GC and two-dimensional GC (114). HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY Polysaccharide CSPs. Warfarin was converted into O-perfluoroacyl derivatives and the enantiomers separated by chiral GC using poly(dimethylsiloxane) anchored with (S)-(-)-1-phenylethylamide (117). R. Analytical Chemistry. A study of enhanced chiral selectivity by the acidic additives ethanesulfonic acid and n-butylamine using a Chiralpak AD column was reported (129). with the phases evaluated including Chiralpak AD and AS. Vol.

A validated chiral HPLC method for the enantiodetermination of rivastigmine hydrogen tartarate was performed on a Chiralcel OD-H column (148). Macrocyclic Antibiotic CSPs. The enantioseparation of trans-chlordane. and the separation efficiencies of the two CSPs were compared. A comparative study between Chiralcel OJ and Chiralcel OD columns was performed on the enantioseparation of imidazole analogues of fluoxetine and miconazole (144). Hepta-Tyr antibiotic-modified silica CSP was used for the enantioseparation of D. and producing baseline separations for 8 compounds in the reversed-phase mode. A Chiralpak IA column was used in the chiral separation of a Ca-sensitizing drug (EMD 53986) (145). Zolmitriptan enantiomers were separated on Chiralpak AD-H CSP (146. A capillary teicoplanin CSP was used in the chiral separation of amino acids derivatized with 7-fluoro-4-nitrobenzoxadiazole in a LC/tandem mass spectrometry method (161). Chiralpak AD column was used in a method for the simultaneous determination of phenylglycidol enantiomers and cinnamyl alcohol (152). A report on transforming chiral LC methodologies into more sensitive LC/electrospray ionization MS without losing enantioselectivity was presented (172). Cellulose and amylose tris(3. A comparative study of teicoplanin. Thalidomide enantiomers were determined in biological samples by HPLC and a vancomycin CSP (167). Analytical Chemistry.L-loxiglumide by CEC and nano-LC methods (175). and the preparative potential of the separation was discussed. Methods of enantioseparation of bicalutamide and its related compounds were investigated on the following CSPs (163): a cellulose-based Chiralcel OD-H. Chiral HPLC methods for the separation of β-lactams were developed using Chiralcel OD-RH and OD-H and Chirobiotic T and TAG (164). Phe and Tyr analogues. An enantioselective HPLC determination of E-6087. 147). The chiral separation of natural and unnatural amino acid derivatives was achieved by micro-HPLC on a ristocetin A CSP (170). The use of native and derivatized CD-based and macrocyclic glycopeptide-based CSPs for the chiral HPLC separation of pterocarpans was investigated by Armstrong et al. exhibiting enantioselectivity for 14 compounds. with baseline resolution being achieved only on the Chiralpak AD (139). Two antibody-based CSPs that have opposing stereoselectivity were used in a study of the effect of the mobile phase on enantioseparation of amino acids (174). Fluoxetine hydrochloride enantiomers were resolved on a Chiralcel OD column (153).or 3-methylsubstituted tetrahydroisoquinoline analogues.5-dimethylphenylcarbamate) CSPs were investigated for the enantioseparation of mirtazapine (143). with the cellulose CSP giving good baseline separations in the normal and polar organic modes. and Chirobiotic R narrow-bore CSPs. Chirobiotic T and TAG were evaluated for the HPLC chiral resolution of unusual amino acids (159). The Chiralpak AD CSP was found to give superior performance compared to Chiralcel OD and Whelk-01 for the enantioseparation of new synthetic pyrrolylphenylethanoneamine monoamino oxidase inhibitor compounds (157). with the better separations obtained by the Chirobiotic TAG column in most cases. and only a few enantiomers separated in the normal-phases mode. Cyclodextrin CSPs and Mobile-Phase Additives. and Chiralcel OJ CSPs (156). The enantiomeric separation of 12 chiral dihydrobenzofurans was achieved on derivatized β-CD CSPs. Separation of the enantiomers of unusual secondary amino acids were investigated on Chirobiotic T and TAG (160). (165). with the hydroxypropyl-β-CD CSP (Cyclobond RSP) being the most effective. Chirobiotic V and V2. Chirobiotic V. 2006 3951 . was validated using a derivatized amylose CSP (154). Seventy-one chiral compounds were enantioresolved on teicoplanin. Chiralpak AD. New aromatase inhibitors containing one chiral center were enantioresolved on cellulose carbamate phase Chiralcel OD-H and cellulose ester phase Chiracel OJ CSP. The enantioseparation of N-protected non-protein amino acid esters by chiral HPLC was achieved on a Chiralcel OD CSP (149). A novel norvancomycin-bonded CSP was synthesized and used to enantioseparate some neutral and basic drugs (173). TAG. ristocetin A. No enantioseparations were observed in the polar organic mode. baseline separating 9 of the 12 compounds. A comparison of various CSPs was made in the direct HPLC enantioseparation of 1. heptachlor epoxide. The enantioseparation of 17 unnatural β-amino acids was achieved using Chirobiotic T (teicoplanin) and TAG (teicoplanin aglycon) CSPs (158). No. β-CD-based Cyclobond I 2000SN. teicoplanin aglycon. A vancomycin CSP was used in a nanoliquid chromatography method for the separation of chlorophenoxy acid herbicides (169). and methylated teicoplanin aglycon was performed using the lowest free energy relationship model (166).5-dimethylphenylcarbamate) CSPs (150). Cyclodextrins continue to enjoy substantial use as CSPs and mobilephase additives. Cellulose tris(3. June 15. with Chiralpak AD CSP giving the best performance (151). and teicoplanin (162). cis-chlordane. with the hydroxypropyl-βCD CSP being the most effective (177). Chiracel OD and Chiralpak AD. and R-hexachlorocyclohexane was investigated on Chiralcel OD. Keilcorin derivatives were enantioresolved using multimodal elution on polysaccharide phases. with the most suitable CSPs determined to be β-CD. teicoplanin aglycon. and preparative enantioseparations were also described (141). Vol. vancomycin. in human plasma. Two vancomycin-based CSPs with different chiral selector coverage. and tert-butyl carbamate-derivatized quinine-based columns.5-dimethylphenylcarbamate) was coated on aminopropyl silica to prepare a CSP for the enantiomeric resolution of triazole pesticides (155). and R. 78. The enantioseparation of 16 racemic dihydrofuroflavones was investigated using CD CSPs (178). 12. with the most effective columns being used in the reversed-phase mode for the derivatized β-CD columns Cyclobond RSP and Cyclobond DM and the γ-CD Cyclobond II. utilizing Chirobiotic T.Separation of the enantiomers of linezolid was compared on derivatized cellulose and amylose columns. heptachlor. a new COX-2 inhibitor. The analytical and semipreparative enantioseparation of albendazole sulfoxide was reported on amylose tris(3. with the carbamate phase giving a better separation (140). were evaluated for enantioresolution of selected drugs including β-blockers and profens (168). and vancomycin in a study of temperature and enantioseparation (171). A study of the separation of enantiomers of 20 isochromene derivatives was performed on native and derivatized CD CSPs (176). The macrocyclic antibiotics were the second most used CSP during this period separating a wide variety of chiral solutes. including unnatural conformationally constrained R-amino acids. macrocyclic glycopeptide-based Chirobiotic T. and β-amino acids having cycloalkane or cycloalkene skeletons. Enantioresolution of tetrahydropalmatine was achieved on Chiralcel OJ-H (142).

S)-Whelk-O1 HPLC CSP was reported by Dungelova et al. were prepared and used to enantioseparate β-adrenergic blockers. Though not as widely used in previous review periods. (209).12-tetracarboxylic acid was prepared and applied to the resolution of various racemic amines (197. and investigation of the enantiodiscrimina3952 tion demonstrated that the enantioselectivity was dependent on the position of the hydroxyl group on the cholestanic backbone. benzodiazepinones. Direct chiral resolution of fungicide benalaxyl was achieved by a (R.5-dichlorobenzoyl amino acids was discussed. A comparison of particle size and flow rate optimization using one-monomer MIPs versus traditional MIPs was investigated by Simon et al. A simple method to prepare a β-CD bonded silica stationary phase containing a propylene short spacer was reported (182) and used to enantioseparate dansyl-amino acids. and 4-alkoxyphenylcarbamic acid 2-methoxy-1-[(4-methylpiperazino)methyl]ethyl ester enantiomers separated on a (S. mono-2A-azido-2A-deoxyperphenylcarbamoylated-β-CD and mono-2A-azido-2A-deoxyperacetylated-β-CD. (187). (208). The chiral separation of the β-blocker drug nadolol was achieved by zone simulated moving bed chromatography (221). A chiral 1. 198). 12. CSPs made of proline peptides were prepared and found to have broad chiral selectivity comparable to that of the Whelk O2 column (207). The use of quinine carbamate-based CSPs was extended from the enantioresolution of chiral acids to neutral polar quinazolone derivatives as reported by Lindner et al. the R1-acid glycoprotein (AGP) was the column of choice for a variety of methods during this review period. and evidence was given in support of a chiral recognition model for the enantioresolution. A HPLC column using N. Two new CSPs based on cholic acid bearing 2-naphthylcarbamate and 3. in which two or three short chiral HPLC columns were connected in series and unresolved enantiomers recycled through the columns until resolution was obtained. and with halogenated solvents (206). with a variety of CSPs used to resolve enantiomers. No. 2006 . the enantio- Analytical Chemistry.S)-Whelk-O1 CSP (210). Miscellaneous CSPs.3. and the mechanism was scrutinized. An affinity monolithic column containing human serum albumin was prepared and evaluated in the chiral resolution of warfarin and tryptophan (186).or 2-chloro-3. A comparison of the thermodynamic properties of particulate and monolithic columns of MIP for the purpose of enantiomeric separations was performed by Kim and Guiochon (215). Quinidine carbamate CSPs were used in the chiral separation of 2. A novel CSP based on (+)-(18crown-6)-2. A CSP covalently bound with chiral pseudo-18-crown-6 ether unit was used in the LC separation of amino compounds in the normal-phase mode (195. There were a number of investigations of MIPs in this review period. (188). June 15. (218).R)-Whelk-O1 CSP (211). A simulated moving columns technique for chiral HPLC was described (220). and antihistamines. flavanone compounds. Selected pyrethroic acids were enantioseparated on cinchona alkaloid-derived CSPs (194). 196).Enantioselective semipreparative HPLC separation of PCB metabolites was examined on various β-CD-based columns (179).5-dinitrobenzoic acid. Enantioseparation of diarylmethanols. and different π-donor aromatic units were used in the enantioseparation of 13 racemic dihydropyrimidonic analytes (214).11. and the overall chiral recognition mechanism was investigated. The direct enantioseparation of racemic β-blockers was investigated on R-Burke 2 CSP and Pirkle 1J CSP (212). polar organic mode. A MIP CSP was used in the screening of oxazepine indole enantiomers (219). and Chiralpak AD and AS in CEC were investigated. and the copolymerization of a quinine tert-butylcarbamate selector monomer with chiral (and achiral) 3. A chiral crown ether column was used to separate amino acid enantiomers by HPLC with inductively coupled plasma carbon emission detection (199). 3-. Methadone and its major metabolites (EDDP and EMDP) were enantioresolved on AGP by a HPLC-MS method (184). Poly(trans-1. Protein-Based CSPs.and reversed-phase versions of the polysaccharide CSPs Chiracel OD and OJ.4-dihydropyridinemonocarboxylic acid was enantioseparated on a tert-butylcarbamoylquinine anion exchanger CSP (192). as was 2-methoxy-2-(1-naphthyl)propionic acid (193). Other thermodynamic studies on the effect of the nature of the organic modifier in chiral chromatography on MIPs (216) and the concentration of the organic modifier were published (217). 191). A new chiral ligand-exchange stationary phase was synthesized and used in the enantioseparation of DL-selenomethionine enantiomers (201). An optimal standing-wave design of nonlinear simulated moving bed systems for enantioseparations was developed (222). The chiral separation of atropine by HPLC was performed on a AGP CSP (183). Two novel CD CSPs. Warfarin enantiomers in human blood plasma were determined on an AGP CSP after liquid/liquid extraction (185). The enantiomeric purity of novel nucleoside analogues was determined using Cyclobond I 2000 and Cyclobond I 2000 RSP (180).2-trifluoro-1-(9anthryl)ethanol (189) and the resolution of phenylpropanol enantiomers (190. When using different background electrolytes and different mobile-phase compositions.2-cyclohexandiylbisacrylamide) CSPs were synthesized and could be used in the normal-phase mode. Vol. The differences exhibited by normal.5-dinitrophenylcarbamate moieties were prepared (203). 78. A new (S)-biotin-bonded silica gel CSP was prepared for HPLC and was used in the enantioseparation of racemic amino acid derivatives (202). and the chiral recognition mechanism was discussed. A biostable L-RNA aptamer CSP was prepared (204) and used to resolve racemates of approximately a dozen related compounds (205).2. and diarylmethyl acetates was performed with the (S.S-dioctyl-o-penicillamine as a chiral ligand-exchange phase (Sumichiral OA-5000) was used for the separation of enantiomers of non-protein amino acids (200). among others (181). The columns showed very high sample capacities and could be used for preparative and semipreparative enantiomeric separations. Synthetic pyrethroid insecticides were enantioresolved on a Sumichiral OA-2500-I CSP (213). Enantioseparation by reversed-phased HPLC with hydrophobic phases made of chiral cationic surfactants was reported by Kurata et al. A strategy to enhance the chiral recognition capacity of polymer-embedded chiral selectors was proposed by Lindner et al. A thermodynamic study of 13 2-. Six new CSPs prepared from 4. CAPILLARY ELECTROCHROMATOGRAPHY The use of CEC remained popular during this review period. diarylmethyl pivalates. L-alanine.

C. Anal.. Fajardo. (47) Lipka. Liq. R. Mmoeller. Daniel.. 25.. (36) Quan. Methods Mol. 35. J. 2004. Kang. Z. A. (5) Patel. Gareil.. 18.. 42.. H. Z. J. Toxicol. C. No. Liu. 2004. 76. (40) Zhao. M. G.. H. Electrophoresis 2005. Chem... Electrophoresis 2004... M. 237-273.. 1-22. van Nyen. received his B. 2005.. 2745-2754. D. 27. Quantification limits in chiral CEC using Chirobiotic V as the CSP were investigated and reported that quantification limits improved 10-fold by utilizing peak compression (234). 31-57.. Environ. 78. (45) Kavalirova. (25) Oi. S. Chromatogr.. R. Len. (9) Roussel.. Chim. Raggi. Vaccher. Richter. C. (224).. 2005. C. Y. Peeters. Rodriguez-Delgado. Saenger-van de Griend.. A. Garcia-Montelongo.-P. 2838-2847. J. 447-498. B. 2004. Picard. Sep. Chromatogr.. Miller. Sci. Arvidsson. Perrin. Chirality 2005. Rabai. E. Wu. 5-12. Technol.. E. Liq. 2735-2744. 2004. D.. Redlich. E.. Electrophoresis 2004. 231-247. Biol. Raggi.. T. V.-M. S. Chromatogr.-P.. M. 2772-2785. J..-P.. 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