Table 1.
Samples and experimental conditions for separations by pH-zone-refining CCC, as reported since 1994.
| Samplea (mass) | Solvent systemsb (volume ratio) | Key reagentc |
Referencesd vol. (year) page | |
|---|---|---|---|---|
| Retainer in SP | Eluter in MP | |||
| Amino acids and peptides | ||||
| DNP-amino acids (0.3 g) | MTBE–AcN–H2O (4:1:5) | TFA (0.04%/UP) | NH3 (0.1%/LP) | JACS 116 (1994) 704 |
| DNP-amino acids (0.7 g | MTBE–H2O | NH3 (22 mM/LP) | TFA (5–20 mM/UP) | JCA 672 (1994) 101 |
| DNP-amino acids (1 g) | MTBE–AcN–H2O (4:1:5) | TFA (200 µl/SS) | NH3 (0.1%/LP) | Mono 1/Ch. 14 (1995) 154 |
| Amino acid-OBzl (0.7 g) | MTBE–H2O | TEA (2.5–40 mM/UP) | HCl (5–40 mM/LP) | JCA 678 (1994) 233 |
| Proline-OBzl (1 g) | MTBE–H2O | TEA (10 mM/UP) | HCl (10 mM/LP) | Mono 1/Ch. 14 (1995) 154 |
| N-CBZ-dipeptides (0.8 g) | MTBE–AcN–H2O (2:2:3) | TFA (16 mM/UP) | NH3 (5.5 mM/LP) | JCA 702 (1995) 197 |
| N-CBZ-tripeptides (0.5 g) | MTBE–AcN–1-BuOH–H2O (2:2:1:5) | TFA (16 mM/UP) | NH3 (2.7 mM/LP) | JCA 702 (1995) 197 |
| Dipeptide-β NA (0.3 g) | MTBE–AcN–H2O (2:2:3) | TEA (5 mM/UP) | HCl (5 mM/LP) | JCA 702 (1995) 197 |
| Dipeptide (2 g) | MTBE–AcN–H2O (4:1:5) | TFA (20 mM/UP)+DEHPA (30–40%/UP) |
HCl (20 mM/LP) | JCA 771 (1997) 81 |
| Bacitracin (5 g) | MTBE–AcN–H2O (4:1:5) | TFA (40 mM/UP) | HCl (20 mM/LP) | JCA 771 (1997) 81 |
| Bovine insulin (0.2 g) | MTBE–H2O | TFA (0.04%/UP) | NH3 (0.1%/LP) | Mono 1/Ch. 14 (1995) 154 |
| Alkaloids | ||||
| Crinine, powelline and | MTBE–H2O | TEA (5 mM/UP) | HCl (5 mM/LP) | JCA 685 (1994) 259 |
| crinamidine (3 g) | MTBE–H2O | HCl (10 mM/LP) | TEA (10 mM/UP) | JCA 685 (1994) 259 |
| Matrin and sophocarpine (2 g) | MTBE–H2O | TEA (10 mM/UP) | HCl (5–10 mM/LP) | JCA 822 (1998) 316 |
| Lappaconitine (10.5 g) | MTBE–THF–H2O (2:2:3) | TEA (10 mM/UP) | HCl (10 mM/LP) | JCA 923 (2001) 281 |
| Vincine and vincamine (0.3 g) | MTBE–H2O | TEA (5 mM/UP) | HCl (5 mM/LP) | JCA 753 (1996) 1 |
| Catecholamines (3 g) | MTBE–H2O | NH4OAc (200 mM/UP)+DEHPA (20%/UP) |
HCl (50 mM/LP) | JCA 724 (1996) 348 |
| Solamargine and solasonine (1 g) | EtOAc–BuOH–H2O (1:4:5) | TEA (5 mM/UP) | TFA (10 mM/LP) | J. Sep. Sci. 32 (2009) 3216 |
| Liensinine, isoliensinine and neferine (2.5 g) | MTBE–H2O | TEA (10 mM/UP) | HCl (5 mM/LP) | J. Sep. Sci .33 (2010) 539 |
| Fangchionoline and tetrandrine (3.5 g) | PE–EtOAc–MeOH–H2O (5:5:1:9) | TEA (10 mM/UP) | HCl (5 mM/LP) | Chromatographia 69 (2009) 959 |
| Sinoacutine (2 g) | Hex–EtOAc–MeOH–H2O (3:7:1:9) | TEA (10 mM/UP) | HCl (5 mM/LP) | JCB ATBLS 879 (2011) 945 |
| N-demethylarmepavine, nucifereine and roemerine (500 mg) | Hex–EtOAc–MeOH–H2O (1:6:1:6) | TEA (10 mM/UP) | HCl (5 mM/LP) | Molecules 16 (2011) 2551 |
| Alstonine, akuammigine, akuammine, picraline, akuammicine and picratidine (500 mg) | MTBE–AcN–H2O (2:2:3) | TEA (pH 10.7/UP) | HCl (pH 1.7/LP) | JLCRT 28 (2005) 775 |
| Caffeine and theophyline (3 g) | MtBE–H2O | TEA (10 mM/UP) | HCl (10 mM/LP) | JLCRT 27 (2004) 365 |
| Berberine, β-hydrodtine canadaline, canaline and isocorypalmine (1.6–2 g) | CHCl3/H2O | HCl (2–25 mM/UP) | TFA (0.05–0.3%/LP) | JJLCRT 24 (2001) 2445 |
| Protopine, corydine, isocorydine and graucine (1 g) | PE–EtOAc–MeOH–H2O (3:7:1:9) | TEA (20 mM/UP) | HCl (5 mM/LP) | JBC 879 (2011) 3767 |
| N-nornuciferine, nuciferine and roemerine (4 g) | PE–EtOAc–MeOH–H2O (5:5:2:8) | TEA (10 mM/UP) | HCl (5 mM/LP) | JCB 878 (2010) 1647 |
| Sicordine, cordine, tetrahydropalmatine, N-methylasimilobine and anonine (1.4 g) | MTBE–AcN–H2O (2:2:3) | TEA (10 mM/UP) | HCl (5 mM/LP) | JCB 878 (2010) 1881 |
| Sinoacutine (2 g) | Hex–EtOAc–MeOH–H2O (3:7:1:9) | TEA (10 mM/UP) | HCl (5 mM/LP) | JCB 879 (2010) 945 |
| Gelsemine, koumine, gelsevirine (1.5 g) | MTBE–AcN–H2O (3:1.5:4) | TEA (20 mM/UP) | HCl (5 mM/LP) | JCA 1218 (2011) 3695 |
| Protopine, tetrahydropalmatine and bicucultine (3.1 g) | MTBE–AcN–H2O (2:2:3) | TEA (5–10 mM/UP) | HCl (5–10 mM/LP) | JCA 1115 (2006) 267 |
| Catharantine, vindorine, vindorinine and vincrystaline (7 g) | MTBE–AcN–H2O (4:1:5) | TEA (10 mM/UP) | HCl (10 mM/LP) | JA 849 (1999) 421 |
| Dyes | ||||
| D&C Orange No. 5 (5 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (0.2 ml/SS) | NH3 (LP/pH 9) | JACS 116 (1994) 704 |
| FD&C Red No. 3 (3 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (0.4 ml/500 ml UP) | NH3 (LP/pH 7.5) | JCA 658 (1994) 505 |
| D&C Red No. 28 (3 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (0.6 ml/500 ml UP | NH3 (LP/pH 8.1) | JCA 678 (1994) 77 |
| D&C Red No. 28 (6 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (1.2 ml/SS) | NH3 (LP/pH 9.2) | JCA 678 (1994) 77 |
| D&C Red No. 22 (5 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (0.8 ml/500 ml UP) | (0.01%/LP) | Mono 2/Ch. 12 (1996) 337 |
| TCF (1 g) | DEE–AcN–10 mM NH4OAc (4:1:5) | TFA (0.25 ml/SS) | NH3 (LP/pH 9.3) | Mono 1/Ch. 16 (1995) 203 |
| TCF (5 g) | MTBE–AcN–H2O (4:1:5) | TFA (0.2 ml/500 ml UP) | NH3 (LP/pH 10.7) | Mono 1/Ch. 16 (1995) 203 |
| Brominated TCF (5 g) | DEE–AcN–H2O (4:1:5) | TFA (24.7 mM/UP) | NaOH (65 mM/LP) | JCA 732 (1996) 283 |
| Rose bengal (1.5 g) | DEE–AcN–H2O (4:1:5) | TFA (5 mM/UP) | NH3 (19.8 mM/LP) | Mono 2/Ch. 12 (1996) 337 |
| Yellow No. 203 (5 g) | isoAmOH–MTBE–AcN–H2O (3:5:1:7) | DA (20%/UP) + H2SO4 (40 mM/SS) |
NH3 (163 mM/LP) | EncSS 6 (2000) 2588 |
| D&C Yellow No. 10 (1.6 g) | isoAmOH–MTBE–AcN–H2O (3:1:1:5) | DA (275 mM/UP) + H2SO4 (38 mM/UP) |
NH3 (80 mM/LP) | JCA 923 (2001) 87 |
| Red No. 106 (0.3 g) | 1-BuOH–H2O | H2SO4 (40 mM/UP) | NH3 (30 mM/LP) | JCA 946 (2002) 157 |
| FD&C Yellow No. 6 (2 g) | MTBE–AcN–H2O (4:1:5) | H2SO4 (0.2%/UP) + TDA (5%/UP) |
NH3 (0.4%/LP) | JCA 753 (1996) 1 |
| Quinoline Yellow (1 g) | isoAmOH–MTBE–AcN–H2O (3:5:1:7) | H2SO4 (18 mmol/SS) + DA (20% in UP) |
NH3 (113 mM/LP) | JCA 1216 (2009) 4161 |
| Quinoline Yellow (5 g) | isoAmOH–MTBE–AcN–H2O (3:5:1:7) | H2SO4 (40 mmol/SS) + DA (20%/UP) |
NH3 (163 mM/LP) | JCA 1216 (2009) 4161 |
| D&C Green No. 8 (20 g) | 1-BuOH–H2O | H2SO4 (0.5%) + DA (20%/UP) |
NaOH (0.1 M/LP) | JCA 1218 (2011) 8249 |
| Tetrachlorofluorecein (5 g) | MTBE–AcN–H2O (4:1:5) | TFA (5.4 mM/UP) | NH3 (15.5 mM/LP) | JLCRT 21 (1998) 183 |
| Isomers | ||||
| MMCCA (0.4 g) | Hex–EtOAc–MeOH–H2O (1:1:1:1) | TFA (1.3 mM/UP) + octanoic acid (3.4 mM/UP) |
NH3 (3.4 mM/LP) | JCA 685 (1994) 253 |
| NCMBA (10 g) | MTBE–AcN–H2O (4:1:5) | TFA (12 mM/UP) | NH3 (100 mM/LP) | JLCRT 21 (1998) 195 |
| NACBA (15 g) | MTBE–AcN–H2O (4:1:5) | TFA (0.32%/UP) | NH3 (0.8%/LP) | JLC 17 (1994) 3507 |
| (±)-DNB-leucine (2 g) | MTBE–H2O | TFA (40 mM/UP) + DPA (40 mM/UP) |
NH3 (20 mM/LP) | JCA 704 (1995) 75 |
| (±)-DNB-valine (2 g) | MTBE–H2O | TFA (40 mM/UP) + DPA (40 mM/UP) |
NH3 (20 mM/LP) | JCA 753 (1996) 1 |
| 3- and 4-Sulfophthalic acids (10 g) | 1-BuOH–H2O | HCl (488 mM/UP) | NH3 (105 mM/LP) | JCA 966 (2002) 111 |
| Caffeoylquinic acids (2 g) | MTBE–AcN–H2O (2:2:3) | TFA (10 mM/UP) | NH3 (8 mM/LP) | JCA 1212 (2008) 48 |
| Dicarboxylic acids (466 mg) | MTBE–AcN–H2O (4:1:5) | TFA (10.8 mM/UP) | NH3 (20.2 mM/LP) | JCA 1151 (2007) 82 |
| Polyphenols | ||||
| NDGA (20 g) | MTBE–H2O | TFA (25 mM/UP) | NaOH (100 mM/LP) | JLCRT 21 (1998) 171 |
| Curcumin (20 g) | MTBE–AcN–H2O (4:1:5) | TFA (20 mM/UP) | NaOH (30 mM/LP) | JLCRT 23 (2000) 2209 |
| Salvanolic acids (2 g) | MTBE–H2O | TFA (10 mM/UP) | NH3 (10 mM/LP) | J. Sep. Sci. 30 (2007) 3214 |
| Cichoric acid (3 g) | MTBE–AcN–H2O (4:1:5) | TFA (10 mM/UP) | NH3 (10 mM/LP) | JCA 1103 (2006) 166 |
| Miscellaneous | ||||
| Hydroxyanthraquinones (1.5 g) | MTBE–THF–H2O (2:2:3) | TFA (10 mM/UP) | NH3 (10 mM/LP) | JCA 1176 (2007) 163 |
| Polyketides (1.68 g) | MiBK–AcN–H2O (4:1:5) | TFA (10 mM/UP) | NaOH (10 mM/LP) | JLCRT 24 (2001) 1775 |
| Coumarin (0.3 g) | MTBE–H2O | TFA (10 mM/UP) | NH3 (20 mM/LP) | JCA 759 (1997) 47 |
| Indole auxins (0.8 g) | MTBE–H2O | TFA (0.04%/UP) | NH3 (0.05%/LP) | JCA 753 (1996) 1 |
| Fucans (0.8 g) | 10% LA in MiBK–25 mM NaOH | JCB 706 (1998) 43 | ||
| Tetrachlorobenzoic acid (1 g) | Hex–EtOAc–MeOH–H2O (6:4:5:5) | TFA (10 mM/UP) | NH3 (10 mM/LP) | JCA (in press) |
a
DNP: dinitrophenyl; CBZ: carbobenzoxy; βNA: naphthylamine; TCF: tetrachlorofluorescein; MMCCA: 1-methyl-4-methoxymethyl cyclohexane carboxylic acid; NCMBA: 2- and 6-nitro-4-chloro-3-methoxybenzoic acid; NACBA: 2- and 6-nitro-3-acetamido-4-chlorobenzoic acid; DNB: dinitrobenzoyl; NDGA: nordihydroguaiaretic acid.
b
MTBE: methyl tert.-butyl ether; AcN: acetonitrile; BuOH: butanol; THF: tetrahydrofuran; DEE: diethyl ether; NH4OAc: ammonium acetate; AmOH: amyl alcohol; Hex: hexane; EtOAc: ethyl acetate; MeOH: methanol; MiBK: methyl isobutyl ketone; LA: liquid amberlite; PE: petroleum-ether.
c
SP: stationary phase; MP: mobile phase; UP: upper phase; LP: lower phase: SS: sample solution; TFA: tetrafluoroacetic acid; TEA: triethylamine; DEHPA: di(2-ethylhexyl)phosphoric acid; DA: dodecylamine; EtOAc: ethyl acetate; TDA: tridodecylamine; DPA: N-dodecanoyl-l-proline-3,5-dimethylanilide (chiral selector).
d
JACS: Journal of American Chemical Society; EncSS: Encyclopedia of Separation Science, 2000 (Editors: I.D. Wilson, E.R. Adlard, M. Cooke, C.F. Poole) Academic Press; JCA: Journal of Chromatography; JLC: Journal of Liquid Chromatography; JLCRT: Journal of Liquid Chromatography and Related Technologies; Mono 1: ACS Monograph on Modern Counter-current Chromatography, 1995 (Editors: W.D. Conway and R.J. Petroski) (Ref. [4]); Mono 2: High-Speed Countercurrent Chromatography, 1996 (Editors: Y. Ito and W.D. Conway) Wiley (Ref. [3]).