Influence of the method of preparation of chiral stationary phases on enantiomer separations in high-performance liquid chromatography

Ihara, Toshihide; Sugimoto, Yoshio; Asada, Makoto; Nakagama, Tatsuro; Hobo, Toshiyuki

doi:10.1016/0021-9673(94)00753-v

Cited by 29 publications

(21 citation statements)

References 14 publications

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“…[30][31][32][33] When residual aminopropyl groups have been suggested to be beneficial for enantioselectivity, no mechanism has been proposed. 34 It is interesting to note that in a recent report Balsells and Walsh 35 demonstrated that achiral ligands can promote chiral catalysis by organometallic complexes. This strategy, called by the authors "amplification of the chiral environment," seems amenable to broader application, practically whenever chiral recognition is an issue.…”

Section: Resultsmentioning

confidence: 98%

Mechanism of chiral recognition in the enantioseparation of 2‐aryloxypropionic acids on new brush‐type chiral stationary phases

et al. 2001

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New brush-type chiral stationary phases (CSP I-IV) comprising N-3,5,6-trichloro-2,4-dicyanophenyl-L-alpha-amino acids (1-4) were prepared by binding of chiral selectors 1-4 to gamma-aminopropyl silica gel. To check the role of excess free aminopropyl groups, CSP V was prepared by binding N-3,5,6-trichloro-2,4-dicyanophenyl-L-alanyl-(3-triethoxysilyl)propylamide to unmodified silica gel. The best separation of racemic 2-aryloxypropionic acids (TR-1-13) was obtained with CSP I; the -(-)-S enantiomer were regularly eluted first, as determined by a CD detector. The mechanism of chiral recognition implies a synergistic interaction of carboxylic acid analyte with the chiral selector and achiral free gamma-aminopropyl units on silica. In fact, CSP V, which is lacking an achiral aminopropyl spacer, shows a lower separation ability for 2-aryloxypropionic acids, but a similar enantioselective discrimination of esters TR-19-20, in comparison with CSP I. CSP I-IV retain unaltered separation ability after a few months of continuous work using a large number of various mobile phases.

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Section: Resultsmentioning

confidence: 98%

Mechanism of chiral recognition in the enantioseparation of 2‐aryloxypropionic acids on new brush‐type chiral stationary phases

et al. 2001

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“…The 3-aminopropyl silica gel was prepared according to the reported, 25 washed thoroughly with Soxlet apparatus. A 50-ml three-necked round bottom flask was charged with 3.56 g dry 3-aminopropyl silica gel, 4.00 g 2 and 16 ml pyridine.…”

Section: Synthesis Of the Csp1-3mentioning

confidence: 99%

“…There are some reports related to the influence of linkage on the enatioseparation ability. [24][25][26][27][28][29][30] Herein, linkage is defined as a spacer and functional group to connect selector to silica gel. Even though a slight change of linkage is made, a significant difference on enantioseparation may be observed.…”

Section: Introductionmentioning

confidence: 99%

Immobilization of (1S,2R)‐(+)‐2‐amino‐1,2‐diphenylethanol derivates on aminated silica gel with different linkages as chiral stationary phases and their enantioseparation evaluation by HPLC

Yin

Liu

et al. 2008

Chirality

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A chiral selector was prepared through the reaction between (1S,2R)-(+)-2-amino-1,2-diphenylethanol and phenyl isocyanate. This selector was immobilized on aminated silica gel, respectively, with bifunctional group linkers of 1,4-phenylene diisocyanate, methylene-di-p-phenyl diisocyanate, and terephthaloyl chloride to produce corresponding three chiral stationary phases. The prepared compounds and chiral stationary phases were characterized by FT-IR, elemental analysis, (1)H NMR, and solid-state (1)H NMR. The enantioseparation ability of these chiral stationary phases was evaluated with structurally various chiral compounds. The chiral stationary phase prepared with 1,4-phenylene diisocyanate as linker showed excellent enantioseparation ability. The influence of different linkages on the enantioseparation was discussed.

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“…22 The capacity of amine was estimated as 1.38 mmol/g, calculated from the nitrogen content of Aminopropylsilica which was available from EA. FT-IR (KBr, cm Above obtained 4 (20.84 g) was dispersed in toluene (60 ml) and MA (55 ml, 0.61 mol) was added.…”

Section: Preparation Of Dendritic Stationary Phasesmentioning

confidence: 99%

Synthesis of dendritic stationary phases with surface‐bonded L‐phenylalanine derivate as chiral selector and their evaluation in HPLC resolution of racemic compounds

Yin

Huang

et al. 2008

Chirality

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Four dendrimers were synthesized on aminopropyl-modified silica gel using methyl acrylate and ethylene diamine as building blocks by divergent method. Four generations of chiral stationary phases (CSPs) were prepared by coupling of L-2-(p-toluenesulfonamido)-3-phenylpropionyl chloride to corresponding dendrimers. The derivatives prepared on silica gel were characterized by FT-IR, (1)H NMR, and elemental analysis. The selector loadings of these four generations of CSPs generally showed a decrease tendency with the increase of generation numbers of dendrimers. The enantioseparation properties of these CSPs were preliminarily investigated by high-performance liquid chromatography. The CSP derived from the three-generation dendrimer exhibited the best enantioseparation capability. Effects of the mobile phase composition and molecular structures of racemic mixtures on enantioseparation were further studied.

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Influence of the method of preparation of chiral stationary phases on enantiomer separations in high-performance liquid chromatography

Cited by 29 publications

References 14 publications

Mechanism of chiral recognition in the enantioseparation of 2‐aryloxypropionic acids on new brush‐type chiral stationary phases

Mechanism of chiral recognition in the enantioseparation of 2‐aryloxypropionic acids on new brush‐type chiral stationary phases

Immobilization of (1S,2R)‐(+)‐2‐amino‐1,2‐diphenylethanol derivates on aminated silica gel with different linkages as chiral stationary phases and their enantioseparation evaluation by HPLC

Synthesis of dendritic stationary phases with surface‐bonded L‐phenylalanine derivate as chiral selector and their evaluation in HPLC resolution of racemic compounds

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