Abstract
Amino acids are very important in our daily life as energy sources and have several functions in metabolism since amino acids are the main key elements for the formation of proteins and peptides. All the amino acids contain a chiral carbon atom and they exist in d- and l-forms except one amino acids, i.e., glycine. Depending upon their d- or l-form, they have different biological activities in living systems. It became evident that the potential biological or pharmacological applications of amino acids are greatly restricted to the one form of the enantiomers. So, the development of methods for their separation has attracted the interest of researchers. In this chapter, we have briefly discussed the separation of amino acids with the help of different chromatographic techniques such as liquid chromatography (LC), gas chromatography (GC), thin-layer chromatography (TLC), and countercurrent chromatography (CCC). Additionally, the role of capillary electrophoresis (CE) has also been discussed toward amino acid separation. To improve the sensitivity, specificity, and applications, chromatographic techniques have been coupled with other analytical techniques, known as hyphenated techniques. In this chapter, the classification of hyphenated techniques and their roles is also discussed in addition to the advantages of chromatographic techniques over the other separation techniques. Chromatographic techniques are simple in handling, fast in the analysis, and can be used for small as well as large-scale separations with good separation efficiency and high accuracy.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- β-CD:
-
β-cyclodextrin
- (S)-NIFE:
-
(S)-N-(4-nitrophenoxycarbonyl)-l-phenylalanine-2-methoxyethyl ester
- ABD-F:
-
4-aminosulphonyl-7-fluro-2,1,3-benzoxadiazol
- ACC:
-
Adsorption column chromatography
- ACN:
-
Acetonitrile
- Ala:
-
Alanine
- Arg:
-
Arginine
- Asn:
-
Asparagine
- Asp:
-
Aspartic acid
- CCC:
-
Counter current chromatography
- CE:
-
Capillary electrophoresis
- CEC:
-
Capillary electro chromatography
- CE-MS:
-
Capillary electrophoresis-mass spectrometry
- CGE:
-
Capillary gel electrophoresis
- CI:
-
Chemical ionization
- CIEF:
-
Capillary isoelectric focusing
- CITP:
-
Capillary isotachophoresis
- CSF:
-
Cerebrospinal fluid
- CSP:
-
Chiral stationary phase
- Cys:
-
Cysteine
- CZE:
-
Capillary zone electrophoresis
- DBD-F:
-
4-(N,N-dimethylaminosulphonyl)-7-fluoro-2,1,3-benzoxadiazole
- DEX:
-
Dextrin
- DM-β-CD:
-
Heptakis (2,6-di-O-methyl)-β-cyclodextrin
- EC:
-
Ethyl chloroformate
- EI:
-
Electron impact ionization
- ESI-MS:
-
Electron spray ionization-mass spectrometry
- FID:
-
Flame ionization detection
- FITC:
-
Fluorescein isothiocyanate
- FLEC:
-
(+)-1-(9-lluorenyl) ethyl chloroformate
- FMOC:
-
Fluorenylmethyloxycarbonyl chloride
- GC:
-
Gas chromatography
- GC-MS:
-
Gas chromatography mass spectrometry
- GLC:
-
Gas liquid chromatography
- Gln:
-
Glutamine
- Glu:
-
Glutamic acid
- Gly:
-
Glycine
- GSC:
-
Gas-solid chromatography
- His:
-
Histidine
- HP-β-CD:
-
Hydroxypropyl-β-cyclodextrin
- HPA-β-CD:
-
6-monodeoxy-6-mono (3-hydroxy)-propylamino-β-cyclodextrin
- HPLC:
-
High performance liquid chromatography
- IE-HPLC:
-
Ion exchange high performance liquid chromatography
- Ile:
-
Isoleucine
- IR:
-
Infrared spectroscopy
- LC:
-
Liquid chromatography
- LC-MS:
-
Liquid chromatography-mass spectrometry
- LC-MS-MS:
-
Liquid chromatography-mass spectrometry-mass spectrometry
- Leu:
-
Leucine
- LIF:
-
Laser induced fluroscence
- LLC:
-
Liquid liquid chromatography
- Lys:
-
Lysine
- Marfey’s reagent:
-
N-α-(2, 4-dinitro-5-fluorophenyl)-l-alaninamide
- MEKC:
-
Micellar electrokinetic chromatography
- MeOH:
-
Methanol
- Met:
-
Methionine
- MRM:
-
Multiple reaction monitoring
- MS:
-
Mass spectrometry
- MTFMPA:
-
Methoxy trifluoromethylphenylacetyl chloride
- NAC:
-
N-acetyl-l cysteine
- NBD:
-
4-fluoro-7-nitrobenzofurazan
- NBD-F:
-
4-fluro-7-nitro-2,1,3-benzoxadiazole
- NBE:
-
n-butyl esters
- NDA:
-
Naphthalene dicarboxaldehyde
- NMR:
-
Nuclear magnetic resonance
- NpF:
-
N-heptaflurobutylryl
- Npf:
-
N-pentafluoropropionyl
- NP-HPLC:
-
Normal phase high performance liquid chromatography
- NRMC:
-
N-(R)-mandelyl-(S)-cysteine
- N-Tfac:
-
N-trifluroacetyl
- OPA:
-
o-phthaldialdehyde
- OS-γ-CD:
-
Octakis (2,3-dihydroxy-6-O-sulfo)-γ-cyclodextrin
- PC:
-
Paper chromatography
- PCC:
-
Partition column chromatography
- Phe:
-
Phenylalanine
- Pro:
-
Proline
- RP-HPLC:
-
Reversed phase high performance liquid chromatography
- RPPC:
-
Reversed phase partition chromatography
- SC-HPLC:
-
Super critical high performance chromatography
- SDS:
-
Sodium dodecyl sulphate
- SE-HPLC:
-
Size exclusion high performance liquid chromatography
- Ser:
-
Serine
- SIM:
-
Selected ion monitoring
- SLC:
-
Solid liquid chromatography
- TEA:
-
Triethanolamine
- TEAA:
-
Tetra ethyl ammonium acetate
- Thr:
-
Threonine
- TLC:
-
Thin layer chromatography
- TLC:
-
Thin layer chromatography
- TM-β-CD:
-
Heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin
- TOF:
-
Time of flight
- TOFR:
-
Time of flight reflection
- Trp:
-
Tryptophan
- Try:
-
Tyrosine
- UPLC-MS/MS:
-
Ultra-performance mass spectroscopy/mass spectroscopy
- UV:
-
Ultraviolet
- Val:
-
Valine
References
Ferreira FD, Rodrigues AL (2008) Separation and purification of amino acids. Diss. Universidade do Porto, Portugal
Cesari M, Rossi GP, Sticchi D, Pessina AC (2005) Is homocysteine important as risk factor for coronary heart disease? Nutr Metab Cardiovasc Dis 15:140–147
Friedman M (1999) Chemistry, nutrition, and microbiology of d-amino acids. J Agric Food Chem 47:3457–3479
Bhushan R, Joshi S (1993) Resolution of enantiomers of amino acids by HPLC. Biomed Chromatogr 7:235–250
Pathak AK (2014) Stabilizing the zwitter-ionic form of amino acids in the gas phase: an ab initio study on the minimum number of solvents and ions. Chem Phys Lett 610:345–350
Hoeprich PD (1965) Alanine: cyeloserine antagonism VI demonstration of d-alanine in the serum of guinea pigs and mice. J Biol Chem 240:1654–1660
Bruckner H, Westhauser T (2003) Chromatographic determination of l- and d-amino acids in plants. Amino Acids 24:43–55
Patzold R, Bruckner H (2006) Gas chromatographic determination and mechanism of formation of d-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell. Amino Acids 31:63–72
Lupke M, Bruckner H (1991) Chiral phase capillary gas chromatography. Chromatographia 31:123–124
Bruckner H, Erbe T (2000) Chromatographic determination of amino acid enantiomers in beers and raw materials used for their manufacture. J Chromatogr A 881:81–91
Rubio Barroso S, Santos Delgado MJ, Martin Olivar C, Polo Diez LM (2006) Indirect chiral HPLC determination and fluorimetric detection of d-amino acids in milk and oyster samples. J Dairy Sci 89:82–89
Ali Mohammed HS, Patzold Bruckner H (2010) Gas chromatographic determination of amino acid enantiomers in bottled and aged wines. Amino Acids 38:951–958
Hamase K, Morikawa A, Etoh S, Tojo Y, Miyoshi Y, Zaitsu K (2009) Analysis of small amounts of d-amino acids and the study of their physiological functions in mammals. Anal Sci 25:961–968
Hashimoto A, Oka T (1997) Free d-aspartate and d-serine in the mammalian brain and periphery. Prog Neurobiol 52:325–353
Gogami Y, Okada K, Oikawa T (2011) High-performance liquid chromatography analysis of naturally occurring d-amino acids in sake. J Chromatogr B 879:3259–3267
Martinez Rodriguez S, Martinez Gomez AI, Rodriguez Vico F, Clemente Jimenez JM, Heras Vazquez L, Javier F (2010) Natural occurrence and industrial applications of d-amino acids: an overview. Chem Biodivers 7:1531–1548
Konya Y, Bamba T, Fukusaki E (2015) Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis. J Biosci Bioeng 121:349–353
Skog DA, Holler FT, Neiman TA (5th ed) (1998) Principles of instrumental analysis. Harcourt Brace College Publisher, Orlando, pp 790, 906 & 947
Lorenzo MP, Dudzik D, Varas E, Gibellini M, Skotnicki M, Zorawski M, Garcia A (2015) Optimization and validation of a chiral GC–MS method for the determination of free d-amino acids ratio in human urine: application to a gestational diabetes mellitus study. J Pharm Biomed Anal 107:480–487
Bhushan R, Bruckner H (2004) Marfey’s reagent for chiral amino acid analysis: a review. Amino Acids 27:231–247
Frank H, Nicholson GJ, Bayer E (1977) Rapid gas chromatographic separation of amino acid enantiomers with a novel chiral stationary phase. J Chromatogr Sci 15:174–176
Frank H, Nicholson GJ, Bayer E (1978) Enantiomer labelling, a method for the quantitative analysis of amino acids. J Chromatogr 167:187–196
Menestrina F, Grisales OJ, Castells CB (2016) Chiral analysis of derivatized amino acids from kefir by gas chromatography. Microchem J 128:267–273
Husek P (1991) Rapid derivatization and gas chromatographic determination of amino acids. J Chromatogr 552:289–299
Pollock GE (1967) Separation of amino acids by gas chromatography using new fluoro derivatives. Anal Chem 39:1194–1196
Fox S, Strasdeit H, Haasmann S, Bruckner H (2015) Gas chromatographic separation of stereoisomers of non-protein amino acids on modified γ-cyclodextrin stationary phase. J Chromatogr A 1411:101–109
Bertrand M, Chabin A, Brack A, Westall F (2008) Separation of amino acid enantiomers VIA chiral derivatization and non-chiral gas chromatography. J Chromatogr A 1180:131–137
Hashimoto A, Nishikawa T, Hayashi T, Fujii N, Harada K, Oka T, Takahashi K (1992) The presence of free d-serine in rat brain. FEBS Lett 296:33–36
Schurig V (1994) Enantiomer separation by gas chromatography on chiral stationary phases. J Chromatogr A 666:111–129
Husek P (1991) Rapid derivatization and gas chromatographic determination of amino acids. J Chromatogr A 552:289–299
Bruckner H, Lupke M (1991) Determination of amino acid enantiomers in orange juices by chiral phase capillary gas chromatography. Chromatographia 31:123–128
Bruckner H, Hausch M (1993) Gas chromatographic characterization of free d-amino acids in the blood serum of patients with renal disorders and of healthy volunteers. J Chromatogr B Biomed Sci Appl 614:7–17
Patzold R, Schieber A, Brückner H (2005) Gas chromatographic quantification of free d-amino acids in higher vertebrates. Biomed Chromatogr 19:466–473
Schieber A, Bruckner H (2001) Ascertainment of d-amino acids in germ free, gnotobiotic and normal laboratory rats. Biomed Chromatogr 15:257–262
Bart HJ, Kostova A (2007) Preparative chromatographic separation of amino acid racemic mixtures I. Adsorpt isotherms. Sep Purif Technol 54:340–348
Fukushima T, Kato M, Santa T, Imai K (1995) Enantiomeric separation and sensitive determination of d, l-amino acids derivatized with fluorogenic benzofurazan reagents on pirkle type stationary phases. Biomed Chromatogr 9:10–17
Bhushan R, Joshi S (1993) Resolution of enantiomers of amino acids by HPLC. Biomed Chromatogr 7:235–250
Vera CM, Shock D, Dennis GR, Farrell W, Shalliker RA (2017) Comparing the selectivity and chiral separation of d- and l-fluorenylmethyloxycarbonyl chloride (FMOC) protected amino acids in analytical High Performance Liquid Chromatography and Supercritical Fluid Chromatography; evaluating throughput, economic and environmental impact. J Chromatogr A 1493:10–18
Toyo’oka T, Imai K (1984) New fluorogenic reagent having halogenobenzofurazan structure for thiols: 4-(aminosulfonyl)-7-fluoro-2, 1, 3-benzoxadiazole. Anal Chem 56:2461–2464
Watanabe Y, Imai K (1981) High-performance liquid chromatography and sensitive detection of amino acids derivatized with 7-fluoro-4-nitrobenzo-2-oxa-1, 3-diazole. Anal Biochem 116:471–472
Toyo’oka T, Suzuki T, Saito Y, Uzu S, Imai K (1989a) Evaluation of benzofurazan derivatives as fluorogenic reagents for thiols and amines using high-performance liquid chromatography. Analyst 114:1233–1240
Pirkle WH, Finn JM, Schreiner JL, Hamper BC (1981) A widely useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers. J A C S 103:3964–3966
Oguri S, Nomura M, Fujita Y (2005) A new strategy for the selective determination of d-amino acids: enzymatic and chemical modifications for pre-column derivatization. J Chromatogr A 1078:51–58
Rubio-Barroso S, Santos-Delgado MJ, MartÃn-Olivar C, Polo-DÃez LM (2006) Indirect chiral HPLC determination and fluorimetric detection of d-amino acids in milk and oyster samples. J Dairy Sci 89:82–89
Goodnough DB, Lutz MP, Wood PL (1995) Separation and quantification of d-and l-phosphoserine in rat brain using Nα-(2, 4-dinitro-5-fluorophenyl)-l-alaninamide (Marfey’s reagent) by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B: Biomed Sci and Appl 672:290–294
Asakura S, Konno R (1997) Origin of d-serine present in urine of mutant mice lacking d-amino-acid oxidase activity. Amino Acids 12:213–223
Nagata Y, Shoji R, Yonezawa S, Oda S (1997) Brain d-serine and tyrosine levels in ataxic mutant mice. Amino Acids 12:95–100
Nagata Y, Borghi M, Fisher GH, D’Aniello A (1995) Free d-serine concentration in normal and Alzheimer human brain. Brain Res Bull 38:181–183
Guranda DT, Kudryavtsev PA, Khimiuk AY, Svedas VK (2005) Efficient enantiomeric analysis of primary amines and amino alcohols by high-performance liquid chromatography with precolumn derivatization using novel chiral SH-reagent N-(R)-mandelyl-(S)-cysteine. J Chromatogr A 1095:89–93
Peter A, Vekes E, Gera L, Stewart JM, Armstrong DW (2002) A comparison of the direct and indirect LC methods for separating enantiomers of unusual glycine and alanine amino acid analogues. Chromatographia 56:S79–S89
Montes Bayon M, B’Hymer C, de Leon CP, Caruso JA (2001) Resolution of seleno-amino acid optical isomers using chiral derivatization and inductively coupled plasma mass spectrometric (ICP-MS) detection Presented at the 2001 European Winter Conference on Plasma Spectrochemistry, Lillehamer, Norway, February 4–8, 2001. JAAS 16:945–950
Peter A, Vekes E, Torok G (2000) 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 52:821–826
Einarsson S, Josefsson B, Moeller P, Sanchez D (1987) Separation of amino acid enantiomers and chiral amines using precolumn derivatization with (+)-1-(9-fluorenyl) ethyl chloroformate and reversed-phase liquid chromatography. Anal Chem 59:1191–1195
Jin D, Miyahara T, Oe T, Toyo’oka T (1999) Determination of d-amino acids labeled with fluorescent chiral reagents, R (2)- and S(1)-4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazoles, in biological and food samples by liquid chromatography. Anal Biochem 269:124–132
Miyazawa T, Minowa H, Imagawa K, Yamada T (1997) Enantiomeric separation of non-protein amino acids by chiral ligand-exchange high-performance liquid chromatography. Anal lett 30:867–882
Remsburg JW, Armstrong DW, Peter A, Toth G (2007) LC enantiomeric separation of unusual amino acids using cyclodextrin-based stationary phases. J Liq Chromatogr Relat Technol 31:219–230
Berkecz R, Ilisz I, Misicka A, Tymecka D, Fulop F, Choi HJ, Peter A (2009) HPLC enantioseparation of β2-homoamino acids using crown ether-based chiral stationary phase. J Sep Sci 32:981–987
Lee T, Lee W, Hyun MH, Park JH (2010) Enantioseparation of α-amino acids on an 18-crown-6-tetracarboxylic acid-bonded silica by capillary electrochromatography. J Chromatogr A 1217:1425–1428
Peter A, Torok G, Armstrong DW (1998) High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase. J Chromatogr A 793:283–296
Zhang X, Bao Y, Huang K, Barnett-Rundlett KL, Armstrong DW (2010) Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases. Chirality: pharmacol Biol Chem Consequences Mol. Asymmetry 22:495–513
Bechtold M, Felinger A, Held M, Panke S (2007) Adsorption behavior of a teicoplanin aglycone bonded stationary phase under harsh overload conditions. J Chromatogr A 1154:277–286
Peter A, Torok G, Armstrong DW, Toth G, Tourwe D (2000) High-performance liquid chromatographic separation of enantiomers of synthetic amino acids on a ristocetin a chiral stationary phase. J Chromatogr A 904:1–15
Peter ALL, Ferenc F, Daniel WA (2001) High-performance liquid chromatographic enantioseparation of β-amino acids. J Chromatogr A 926:229–238
Peter A, Vekes E, Arki A, Toure D, Lindner W (2003) Direct high-performance liquid chromatographic enantioseparation of α-substituted proline analogues on a quinine-derived chiral anion-exchanger stationary phase. J Sep Sci 26:1125–1132
Miyazawa T, Shindo Y, Yamada T, Kuwata S (1993) Enantiomeric separation of N-protected non-protein amino acid esters by chiral high-performance liquid chromatography. Anal Lett 26:457–473
Lee KA, Yeo S, Kim KH, Lee W, Kang JS (2008) Enantioseparation of N-fluorenylmethoxycarbonyl & #x03B1;-amino acids on polysaccharide-derived chiral stationary phases by reverse mode liquid chromatography. J Pharm Biomed Anal 46:914–919
Huanga XY, Peja D, Liua JF, Dia LD (2018) A review on chiral separation by counter-current chromatography: development, applications and future outlook. J Chromatogr A 1531:1–12
Ito Y (2005) Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J Chromatogr A 1065:145–168
Gavioli E, Maier NM, Minguillon C, Lindner W (2004) Preparative enantiomer separation of dichlorprop with a cinchona-derived chiral selector employing centrifugal partition chromatography and high-performance liquid chromatography: a comparative study. Anal Chem 76:5837–5848
Sutherland I, Hewitson P, Ignatova S (2009) Scale-up of counter-current chromatography: demonstration of predictable isocratic and quasi-continuous operating modes from the test tube to pilot/process scale. J Chromatogr A 1216:8787–8792
Bhushan R, Martens J (1997) Direct resolution of enantiomers by impregnated TLC. Biomed Chromatogr II: 280–285
Sherma J, Fried B (3rd ed, revised and expanded) (2005) Handbook of Thin-Layer Chromatography. Lafayette College Easton, Pennsylvania, U.S.A
Bhushan R, Ali I (1987) Resolution of enantiomeric mixtures of phenylthiohydantoin amino acids on (+)-tartaric acid-impregnated silica gel plates. J Chromatogr 392:460–463
Borke ML, Kirch ER (1953) Separation of some of the opium alkaloids by surface chromatography. J Am Pharm Assoc Sci Ed 42:627–629
Korzun BP, Dorfman L, Brody SM (1963) Separation of sonne alkaloids, steroids, and synthetic compounds by thin-layer chromatography. Anal Chem 35:950
Sherma J, kowalska T (2006) Preparative layer chromatography
Alak A, Armstrong DW (1986) Thin-layer chromatographic separation of optical, geometrical, and structural isomers. Anal Chem 58:582–584
Grinberg N, Weinstein S (1984) Enantiomeric separation of Dns-amino acids by reversed-phase thin layer chromatography. J Chromatogr A 303:251–255
Virtanen R, Kivalo P (1969) Quantitative high-voltage zone electrophoresis method. Suomen Kemistilehti B 42:182
Jorgensen JW, Lukacs KD (1981) Zone electrophoresis is open-tubular glass capillaries. Anal Chem 53:1298–1302
Whatley H (2001) Basic principles and modes of capillary electrophoresis. In: Clinical and forensic applications of capillary electrophoresis. Humana Press, Totowa, NJ pp 21–58
Tsunoda M, Kato M, Fukushima T, Santa T, Homma H, Yanai H, Soga T, Imai K (1999) Determination of aspartic acid enantiomers in bio-samples by capillary electrophoresis. Biomed Chromatogr 13:335–339
Thorsen G, Engstrom A, Josefsson B (1997) Enantiomeric determination of amino compounds with high sensitivity using the chiral reagents (+)- and (−)-1-(9-anthryl)-2-propyl chloroformate. J Chromatogr A 786:347–354
Teruhisa Ueda, Kitmura F, Mitchell R, Metcalf T, Kuwana T, Nakamoto A (1991) Chiral separation of naphthalene-2,3-dicarboxaldehyde-labeled amino acid enantiomers by cyclodextrin-modified micellar electrokinetic chromatography with laser-induced fluorescence detection. Anal Chem 63:2979–2981
Cole OR, Sepaniak JM, Hinze WL (1990) Optimization of binaphthyl enantiomer separations by capillary zone electrophoresis using mobile phases containing bile salts and organic solvent. J High Resolut Chromatogr 13:579–582
Otsuka K, Kawahara L, Tatekawa K, Terabe S (1991) Chiral separations by micellar electrokinetic chromatography with sodium N-dodecanoyl-l-valinate. J Chromatogr 559:209–214
Kuhn R, Stoecklin F, Erni F (1992) Chiral separations by host-guest complexation with cyclodextrin and crown ether in capillary zone electrophoresis. Chromatographia 33:32–36
Tsunoda M, Kato M, Fukushima T, Santa T, Homma H, Yanai H, Soga T, Imai K (1999) Determination of aspartic acid enantiomers in bio-samples by capillary electrophoresis. Biomed Chromatogr 13:335–339
Tsunoda M, Kato M, Fukushima T, Santa T, Homma H, Yanai H, Soga T, Imai K (1999) Determination of aspartic acid enantiomers in bio-samples by capillary electrophoresis. Biomed Chromatogr 13:335–339
Zhao S, Yuan H, Xiao D (2005) Detection of d-Serine in rat brain by capillary electrophoresis with laser induced fluorescence detection. J Chromatogr B A 822:334–338
Wagner Z, Tabi T, Jako T, Zachar G, Csillag A, Szoko E (2012) Chiral separation and determination of excitatory amino acids in brain samples by CE-LIF using dual cyclodextrin system. Anal Bioanal Chem 404:2363–2368
Jako T, Szabo E, Tabi T, Zachar G, Csillag A, Szoko E (2014) Chiral analysis of amino acid neurotransmitters and neuromodulators in mouse brain by CE-LIF. Electrophoresis 35:2870–2876
Lorenzo MP, Villasenor A, Ramamoorthy A, Garcia A (2013) Optimization and validation of a capillary electrophoresis laser-induced fluorescence method for amino acids determination in human plasma: Application to bipolar disorder study. Electrophoresis 34:1701–1709
Singh NS, Paul RK, Sichler M, Moaddel R, Bernier M, Wainer IW (2012) Capillary electrophoresis–laser-induced fluorescence (CE-LIF) assay for measurement of intracellular d-serine and serine racemase activity. Anal Biochem 421:460–466
Zhao S, Liu YM (2001) Electrophoretic separation of tryptophan enantiomers in biological samples. Electrophoresis 22:2769–2774
Zhao S, Feng Y, LeBlanc MH, Liu YM (2001) Determination of free aspartic acid enantiomers in rat brain by capillary electrophoresis with laser-induced fluorescence detection. J Chromatogr B Biomed Sci Appl 762:97–101
Li H, Li C, Yan ZY, Yang J, Chen H (2010) Simultaneous monitoring multiple neurotransmitters and neuromodulators during cerebral ischemia/reperfusion in rats by microdialysis and capillary electrophoresis. J Neurosci Methods 189:162–168
Fradi I, Servais AC, Lamalle C, Kallel M, Abidi M, Crommen J, Fillet M (2012) Chemo-and enantio-selective method for the analysis of amino acids by capillary electrophoresis with in-capillary derivatization. J Chromatogr A 1267:121–126
Londhe SV, Mulgund SV, Chitre TS, Mallade PS, Barival JB, Jain KS (2008) Hyphenated techniques in analytical world. Indian J Pharm educ Res dec 42:4
Kalpesh NP, Jayvadan KP, Manish PP, Ganesh CR, Hitesh AP (2010) Introduction to hyphenated techniques and their applications in pharmacy. Pharm Methods 1:2–13
Phalke P, Kavade S (2013) Review on hyphenated techniques. Int J Chem Stud 1:157–165
Singh S, Handa T, Narayanam M, Sahu A, Junwal M, Shah RP (2012) A critical review on the use of modern sophisticated hyphenated tools in the characterization of impurities and degradation products. J Pharm Biomed Anal 69:148–173
Guo X, Lankmayr E (2012) Hyphenated techniques in gas chromatography. In: Advanced gas chromatography-progress in agricultural, biomedical and industrial applications. InTech
Bruckner H, Schieber A (2000) Determination of free d-amino acids in mammalia by chiral gas chromatography-mass spectrometry. J Sep Sci 23:576–582
Culea M, Iordache AM, Horj E, Mesaros C, Bleiziffer R (2016) GC-MS Methods for amino acids determination in different biological extracts. Studia Ubb Chemia LXI 61:213–222
Patzold R, Schieber A, Brückner H (2005) Gas chromatographic quantification of free d-amino acids in higher vertebrates. Biomed Chromatogr 19:466–473
Schieber A, Bruckner H (2001) Ascertainment of d-amino acids in germ free, gnotobiotic and normal laboratory rats. Biomed Chromatogr 15:257–262
Hashimoto A, Nishikawa T, Oka T, Hayashi T, Takahashi K (1993) Widespread distribution of free d-aspartate in rat periphery. FEBS Lett 331:4–8
Hasegawa H, Shinohara Y, Masuda N, Hashimoto T, Ichida K (2011) Simultaneous determination of serine enantiomers in plasma using mosher’s reagent and stable isotope dilution gas chromatography-mass spectrometry. J Mass Spectrom 46:502–507
Waldhier MC, Almstetter MF, Nurnberger N, Gruber MA, Dettmer K, Oefner PJ (2011) Improved enantiomer resolution and quantification of free d-amino acids in serum and urine by comprehensive two-dimensional gas chromatography-time-of-flight mass spectrometry. J Chromatogr A 1218:4537–4544
Patzold R, Schieber A, Bruckner H (2005) Gas chromatographic quantification of free d-amino acids in higher vertebrates. Biomed Chromatogr 19:466–473
Bruckner H, Schieber A (2001) Determination of amino acid enantiomers in human urine and blood serum by gas chromatography-mass spectrometry. Biomed Chromatogr 15:166–172
Schieber A, Bruckner H, Rupp-Classen M, Nowitzki-Gfimm S, Classen HG (1997) Evaluation of d-amino acid levels in rat by gas chromatography-selected ion monitoring mass spectrometry: no evidence for subacute toxicity of orally fed d-proline and d-aspartic acid. J Chromatogr B Biomed Sci Appl 69:1–12
Jin D, Miyahara T, Oe T, Toyo’oka T (1999) Determination of d-amino acids labeled with fluorescent chiral reagents, R (−)-and S (+)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2, 1, 3-benzoxadiazoles, in biological and food samples by liquid chromatography. Anal Biochem 269:124–132
Konya Y, Bamba T, Fukusaki E (2016) Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis. J Biosci Bioeng 121:349–353
Rojas C, Alt J, Ator NA, Thomas AG, Wu Y, Hin N, Slusher BS (2016) d-amino-acid oxidase inhibition increases d-serine plasma levels in mouse but not in monkey or dog. Neuropsychopharmacology 41:1610
Sakamoto T, Kuwabara R, Takahashi S, Onozato M, Ichiba H, Iizuka H, Fukushima T (2016) Determination of d-serine in human serum by LC-MS/MS using a triazole-bonded column after pre-column derivatization with (S)-4-(3-isothiocyanatopyrrolidin-1-yl)-7-(N, N-dimethylaminosulfonyl)-2, 1, 3-benzoxadiazole. Anal Bioanal Chem 408:517–526
Xie Y, Alexander GM, Schwartzman RJ, Singh N, Torjman MC, Goldberg ME, Moaddel R (2014) Development and validation of a sensitive LC–MS/MS method for the determination of d-serine in human plasma. J Pharm Biomed Anal 89:1–5
Nagata Y, Higashi M, Ishii Y, Sano H, Tanigawa M, Nagata K, Urade M (2006) The presence of high concentrations of free d-amino acids in human saliva. Life Sci 78:1677–1681
Ohnuma T, Sakai Y, Maeshima H, Hatano T, Hanzawa R, Abe S, Arai H (2008) Changes in plasma glycine, L-serine, and d-serine levels in patients with schizophrenia as their clinical symptoms improve: results from the Juntendo University Schizophrenia Projects (JUSP). Prog Neuropsychopharmacol Biol Psychiatry 32:1905–1912
Berna MJ, Ackermann BL (2007) Quantification of serine enantiomers in rat brain microdialysate using Marfey’s reagent and LC/MS/MS. J Chromatogr B 846:359–363
Fuchs SA, de Barse MM, Roeleveld MW, Hendriks M, Dorland L, Klomp LW, de Koning TJ (2008) Two mass-spectrometric techniques for quantifying serine enantiomers and glycine in cerebrospinal fluid: potential confounders and age-dependent ranges. Clin Chem 54:1443–1450
Luykx JJ, Bakker SC, Van Boxmeer L, Vinkers CH, Smeenk HE, Visser WF, Van Dongen EP (2013) d-amino acid aberrations in cerebrospinal fluid and plasma of smokers. Neuropsychopharmacology 38:2019
Xing Y, Li X, Guo X, Cui Y (2016) Simultaneous determination of 18 d-amino acids in rat plasma by an ultrahigh-performance liquid chromatography-tandem mass spectrometry method: application to explore the potential relationship between Alzheimer’s disease and d-amino acid level alterations. Anal Bioanal Chem 408:141–150
Mochizuki T, Takayama T, Todoroki K, Inoue K, Min JZ, Toyooka T (2015) Towards the chiral metabolomics: Liquid chromatography–mass spectrometry based dl-amino acid analysis after labeling with a new chiral reagent, (S)-2, 5-dioxopyrrolidin-1-yl-1-(4, 6-dimethoxy-1, 3, 5-triazin-2-yl) pyrrolidine-2-carboxylate, and the application to saliva of healthy volunteers. Anal Chim Acta 875:73–82
Karakawa S, Shimbo K, Yamada N, Mizukoshi T, Miyano H, Mita M, Hamase K (2015) Simultaneous analysis of d-alanine, d-aspartic acid, and d-serine using chiral high-performance liquid chromatography-tandem mass spectrometry and its application to the rat plasma and tissues. J Pharm Biomed Anal 115:123–129
Sugimoto H, Kakehi M, Jinno F (2015) Bioanalytical method for the simultaneous determination of d-and l-serine in human plasma by LC/MS/MS. Anal Biochem 487:38–44
Kinoshita K, Jingu S, Yamaguchi JI (2013) A surrogate analyte method to determine d-serine in mouse brain using liquid chromatography–tandem mass spectrometry. Anal Biochem 432:124–130
Fukushima T, Kato M, Santa T, Imai K (1995) Enantiomeric separation and sensitive determination of D, L-amino acids derivatized with fluorogenic benzofurazan reagents on pirkle type stationary phases. Biomed Chromatogr 9:10–17
Konya Y, Bamba T, Fukusaki E (2015) Extra-facile chiral separation of amino acid enantiomers by LC-TOFMS analysis. J Biosci Bioeng 121:349–353
Song Y, Feng Y, LeBlanc MH, Zhao S, Liu YM (2006) Assay of trace d-amino acids in neural tissue samples by capillary liquid chromatography/tandem mass spectrometry. Anal Chem 78:8121–8128
Xie Y, Alexander GM, Schwartzman RJ, Singh N, Torjman MC, Goldberg ME, Moaddel R (2014) Development and validation of a sensitive LC-MS/MS method for the determination of d-serine in human plasma. J Pharm Biomed Anal 89:1–5
Van der Greef J, Niessen WMA (1992) Hyphenated methods in mass spectrometry. Int J Mass Spectrom Ion Processes 12:857–873
Niessen WMA, Tjaden UR, van der Greef J (1993) Capillary electrophoresis-mass spectrometry. J Chromatogr 636:3–19
Diaz MDC, d’Orly F, Granados SG, de Leon-Rodriguez LM, Varenne A (2016) Design, synthesis, and characterization of new cyclic D, L-α-alternate amino acid peptides by capillary electrophoresis coupled to electrospray ionization mass spectrometry. Anal Chem 502:8–15
Garcia F, Henion JD (1992) Gel-filled capillary electrophoresis/mass spectrometry using a liquid junction ion spray interface. Anal Chem 64:985–990
Lu W, Yang G, Cole RB (1995) Determination of amino acids by on-line capillary electrophoresis-electrospray ionization mass spectrometry. Electrophoresis 16:487–492
Soga T, Heiger DN (2000) Amino acid analysis by capillary electrophoresis electrospray ionization mass spectrometry. Anal Chem 72:1236–1241
Acknowledgements
Mr. Majhi has given the major contribution in writing this chapter along with drawing the figures and tables, taking the copyright permission, etc.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Majhi, K.C., Karfa, P., Madhuri, R. (2019). Chromatographic Separation of Amino Acids. In: Inamuddin (eds) Applications of Ion Exchange Materials in Biomedical Industries. Springer, Cham. https://doi.org/10.1007/978-3-030-06082-4_4
Download citation
DOI: https://doi.org/10.1007/978-3-030-06082-4_4
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-06081-7
Online ISBN: 978-3-030-06082-4
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)