• 综述 •
汤波, 王微, 罗爱芹. 新型多孔材料用作色谱手性固定相[J]. 化学进展, 2022, 34(2): 328-341.
Bo Tang, Wei Wang, Aiqin Luo. New Porous Materials Used as Chiral Stationary Phase for Chromatography[J]. Progress in Chemistry, 2022, 34(2): 328-341.
手性固定相是色谱法分离分析手性化合物的关键。近年来,随着材料科学的迅速发展,越来越多的新型手性材料被作为色谱固定相用于手性分离分析。本文综述了近5年来液相色谱、气相色谱和毛细管电色谱领域的新型手性固定相的研究进展,重点总结了基于手性多孔材料的新型手性固定相研究,最后对手性固定相的研究进行了总结与展望。
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No. | Racemate | α | Rs | ref |
---|---|---|---|---|
1 | 1-(1-naphthyl)ethanol | 5.70 | 4.55 | |
2 | 1-Phenyl-1-propanol | 1.33 | 2.47 | |
3 | α-Methylbenzylamine | 2.00 | 2.35 | |
4 | 1,1'-Bi-2-naphthol | 3.96 | 2.31 | |
5 | trans-stilbene oxide | 7.24 | 4.09 | |
6 | DL-Mandelic acid | 2.75 | 3.00 | |
7 | DL-malic acid | 1.78 | 2.57 | |
8 | DL-Tyrosine | 2.16 | 1.64 | |
9 | DL-Cysteine | 2.46 | 1.91 | |
10 | DL-Phenylalanine | 2.24 | 1.73 | |
11 | DL-Threonine | 1.68 | 2.08 | |
12 | DL-Histidine | 2.11 | 1.74 | |
13 | Benzoin | 1.57 | 3.71 | |
14 | Zopiclone | 6.74 | 2.24 | |
15 | Omeprazole | 1.53 | 2.57 | |
16 | Ofloxacin | 1.78 | 2.36 | |
17 | Chlorpheniramin | 2.17 | 2.07 | |
18 | Naproxen | 7.55 | 3.53 | |
19 | Ibuprofen | 3.54 | 2.03 | |
20 | Praziquantel | 3.29 | 2.14 |
ref Racemates | Resolution (Rs) | |||||||
---|---|---|---|---|---|---|---|---|
115 | 116 | 118 | 119 | 120 | 121 | 122 | 123 | |
1-(Naphthalen-1-yl)ethanol | - | - | - | - | - | - | 1.13 | - |
Alprenlol | - | - | - | - | - | 1.11 | - | - |
Arginine | - | - | - | - | 2.85 | - | - | - |
Atenolol | - | - | 2.15 | - | 2.97 | - | - | - |
Azelastine | - | - | 2.1 | - | - | - | - | - |
Bendroflumethiazide | - | - | - | - | - | - | 1.02 | - |
Benzoin | - | - | - | - | - | 3.35 | 0.63 | 1.71 |
Bisoprolol | - | - | 1.88 | - | - | - | - | - |
Dns-DL-leucine | - | 2 | - | - | - | - | - | - |
Dns-DL-phenylalanine | - | 2.24 | - | - | - | - | - | - |
Dns-DL-serine | - | 1.4 | - | - | - | - | - | - |
Dns-DL-threonine | - | 1.75 | - | - | - | - | - | - |
Dns-DL-valine | - | 1.96 | - | - | - | - | - | - |
Epinephrine | 1.36 | - | - | - | - | - | - | - |
Esmolol | - | - | 2.13 | 1.51 | - | - | - | - |
Flavanone | - | - | - | - | - | - | 0.56 | - |
Furoin | - | - | - | - | - | 1.42 | 1.18 | 1.35 |
Isoprenaline | 1.61 | - | - | - | - | - | - | - |
Ketoprofen | - | - | - | - | - | - | 1.34 | - |
Labetalol | - | - | 0.58 | - | 1.95 | - | - | - |
Lysine | - | - | - | - | 1.48 | - | - | - |
Mandelic acid | - | - | - | - | - | - | 0.56 | 1.79 |
Metoprolol | - | - | 1.58 | 1.53 | - | - | - | - |
Ofloxacin | - | - | - | - | - | - | 0.86 | - |
Omeprazole | - | - | - | - | - | - | 2.23 | - |
Propranolol | - | - | 1.73 | 1.57 | - | - | - | - |
Salbutamol | - | - | - | 2.08 | - | - | - | - |
Sotalol | - | - | - | 2.14 | 3.9 | - | - | - |
Synephrine | 2.03 | - | - | - | - | - | - | - |
Terbutaline | 2.09 | - | - | - | - | - | - | - |
Terbutaline | - | - | - | 1.7 | - | - | - | - |
trans-stilbene oxide | - | - | - | - | - | - | 1.58 | - |
Tryptophan | - | - | - | - | 1.62 | - | - | - |
Tyrosine | - | - | - | - | 1.81 | - | - | - |
Warfarin | - | - | 1.57 | - | - | - | 0.66 | - |
Types | Types of materials | Name of CSPs | Main separation analytes | ref |
---|---|---|---|---|
HPLC | CMOFs | [Cd2(d-cam)3] ·2Hdma·4dma | alcohol, naphthol, ketone, and base compounds | |
γ-CDMOF | aromatic alcohol | |||
[Zn(L-tyr)]n(L-tyrZn) | alcohols, amines, ketones, ethers, organic acids | |||
[Zn4(btc)2(Hbtc)(L-His)2(H2O)4]·1.5H2O | ||||
{[Zn2(L-trp)2(bpe)2(H2O)2] ·2H2O·2NO3}n | ||||
[Co2(L-Trp)(INT)2(H2O)2(ClO4)] | ||||
[Co2(sdba)((L-Trp)2] | ||||
[Co(L-Glu)(H2O)·H2O]∞ | ||||
[Cu(H2O)2(S-TA)2]·6H2O | ibuprofen, benzoin, furoin, thalidomide, trans-2,3- Diphenyloxirane, 1-phenyl-ethan-1-ol, and flavanone | |||
[Zn(BDA)(bpe)]·2DMA | sulfoxides, sec-alcohols and flavanones | |||
[Zn(BDA)(bpa)]·2DMA | ||||
(R)-CuMOF-2 | sec-alcohols, sulfoxides, epoxides, lactone, 1,3-dioxolan-2-one, and oxazolidinone | |||
[Zn[(R)-1]2(NMF)2]·NMF | sulfoxides, sec-alcohols, β-lactams, benzoins, flavanones and epoxides | |||
[Nd3(D-cam)8(H2O)4Cl]n | alcohols, amines, ketones, α-amino acids | |||
D-his-ZIF-8@SiO2 | alcohol, phenol, amine, ketone, and organic acid | |||
Cu2((+)-Cam)2Dabco@SiO2 | carboxylic acid, ketones and phenols | |||
[Zn2(bdc)(L-lac)(dmf)](DMF) | (±)-methyl phenyl sulfoxide | |||
CCOFs | BtaMth@SiO2 | nitrotoluene, nitrochlorobenzene, beta-cypermethrin, metconazole | ||
biomolecule⊂COF 1 | DL-tryptophan, DL-leucine, DL-threonine, DL-lysine, DL-aspartic acid, ofloxacin, propranolol hydrochloride, metoprolol tartrate, alanyl glutamine, chlorpheniramine, benzoin | |||
(R, R)-CCOF-6 | 1-phenyl-2-propanol, 1-phenyl-1-pentanol, 1-phenyl-1-propanol and 1-(4-bromophenyl)ethanol | |||
CMSs | HOCMS (C14-L-AlaA) | alcohols, ketones, amines, aldehydes and organic acids | ||
CMPs | MP-CDPs | 1-phenyl-1-propanol, 3-chloro-1-phenyl -1-propanol, mandelic acid, D/L-prolinol | ||
GC | CMOFs | MIL-101(Al)-Xs (Xs=S-2-Ppa, R-Epo, (+)-Ac-l-Ta, l-Pro, 1S-(+)-Cam) | alcohols, amines, nitriles, esters and aldehydes | |
CMOM-3S | aromatic alcohols and nitriles | |||
PSO/CCS-3S | aromatic alcohols, amines, nitriles, lactones, organic acid | |||
CPOCs | CC3-R/CC3-S | chiral alcohols and amines | ||
CC3-R | chiral alcohols, diols, amines, alcohol amines, esters, ketones, ethers, halohydrocarbons, organic acids, amino acid methyl esters, and sulfoxides | |||
CC10 | chiral alcohols, esters, ketones, ethers, halohydrocarbons, epoxides, and organic acids | |||
CC9 | chiral alcohols, esters, ethers and epoxides | |||
CC5 | derivatized amino acids, alcohols, alcohol amines, esters, ethers, ketones, and epoxides | |||
POC-1 | alcohols, diols, esters, lactones, halohydrocarbons, ethers, epoxides, ketones and sulfoxides | |||
CC9-OH | alcohols, diols, halohydrocarbons, epoxides, esters, lactones, ketones, ethers, and organic acids | |||
CC3R-OH | chiral alcohols | |||
CMOCs | [Zn3L2] | alcohols, diols, epoxides, ethers, halohydrocarbons, and esters | ||
aMOP-A | chiral alcohols, ethers, organic acids, amino acid derivatives | |||
MOC-PA | ethers, organic acids, ethers, amino acid derivatives | |||
CCOFs | CTpPa-1 | (±)-1-phenylethanol; (±)-1-phenyl-1-propanol; (±)-limonene; (±)-methyl lactate | ||
CMS | HOCMS (C14-L-AlaA) | chiral alcohols, aldehydes, esters, organic acids, epoxides, and amino acid derivatives | ||
HOCMS (C14-L-Val) | chiral alcohols, epoxides and amino acid derivatives | |||
CMONs | MON-TGC/MON-MSA/MON-NAC | chiral alcohols | ||
CEC | CMOFs | [Zn2(D-Cam)2(4,4'-bpy)]n | DL-Phenylalanine, DL-Tyrosine | |
JLU-Liu23 | epinephrine, isoprenaline, synephrine, terbutaline | |||
Cu-SD@PD | chiral Dns-amino acids | |||
BSA@ZIF-8 | epicatechin/catechin and salbutamol | |||
CCOFs | cellulase@poly(GMA-EDMA-SNW-1) | (±)-atenolol,(±)-Metoprolol, (±)-bisoprolol,(±)-propranolol, (±)-esmolol,(±)-azelastine,(±)-warfarin, (±)-labetalol | ||
β-CD COF | (±)-sotalol, (±)-terbutaline, (±)-propranolol, (±)-Metoprolol, (±)-salbutamol and (±)-esmolol | |||
MDI-β-CD-modified COF | tryptophan, tyrosine, arginine, lysine, atenolol, labetalol, sotalol, and celiprolol | |||
CPOCs | CC3-R | furoin, benzoin, alprenlol | ||
CMOCs | Zn3 | Ofloxacin, Furoin, Benzoin, Omeprazole, Bendroflumethiazide | ||
Zn3 | Warfarin sodium, Ofloxacin, Mandelic acid, Ketoprofen | |||
[Fe4 ](ClO4)8·Solvent | Ofloxacin, 1-(Naphthalen-1-yl)ethanol, Flavanone, Trans-stilbene oxide | |||
Zn3L2@poly(IL-co-EDMA) | mandelic acid, benzoin, furoin |
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