Insights into chromatographic enantiomeric separation of allenes on cellulose carbamate stationary phase

Ma, Shengli; Tsui, Hung‐Wei; Spinelli, Earl; Busacca, Carl A.; Franses, Elias I.; Wang, Nien‐Hwa Linda; Wu, Ling; Lee, Heewon; Senanayake, Chris H.; Yee, Nathan K.; Gonella, Nina; Fandrick, Keith R.; Grinberg, Nelu

doi:10.1016/j.chroma.2014.08.032

Cited by 29 publications

(20 citation statements)

References 30 publications

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“…Results in Table 4 and Table 5 show that there exists linear relationship between ln a, ln k 1 , ln k 2 and 1/T. ln k 1 and ln k 2 decrease as the column temperature rises, which means the interaction between CSP and enantiomers is exothermic in nature and the enantioseparation is enthalpy dominated according to the previous studies of enantioseparation [24,25]. The Van't Hoff curve is basically linear, and the selectivity factor (α) is also a straight line (R 2 > 0.98), which shows enantioselective interactions and retention mechanism of the enantiomers on chiral stationary phase do not change obviously with chromatographic separation temperature.…”

Section: ∆(δG) = ∆(δH)-t∆(δs)mentioning

confidence: 72%

Chiral Stationary Phases and their Relationship with Enantiomer Structures in Enantioseparation Research of Analytical Laboratory

Song

Zhang

et al. 2017

J. Mex. Chem. Soc.

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Chiral stationary phases (CSPs) and molecular structure of enantiomers are two independent but related aspects in enantioseparation, which are discussed on the basis of the experimental data from the previous study. Two enantioseparation experiments are performed to illustrate the relationship between enantiomer structures and chiral stationary phases, one is the resolution of mandelic acid derivatives and the other is about prasugrel. Thermodynamic mechanism and theoretical study with computational chemistry method is helpful to understand the interactions of enantiomer and CSPs.

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Section: ∆(δG) = ∆(δH)-t∆(δs)mentioning

confidence: 72%

Chiral Stationary Phases and their Relationship with Enantiomer Structures in Enantioseparation Research of Analytical Laboratory

Song

Zhang

et al. 2017

J. Mex. Chem. Soc.

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“…The peaks at 1743–1721 cm −1 correspond to the ester in carbamate residue, in which the peak shapes of CS1 and CS3 are similar, and the ones of CS2 and CS4 are also similar. The peaks in the region of 1549–1546 cm −1 are assigned to the absorption of amide II resulting from 60% N–H bending vibration and 40% C–N stretching vibration . The peaks of CS1 and CS3 split a little at 1533 cm −1 for CS1 and at 1518 cm −1 for CS3, but do not split for CS2 and CS4.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation characteristics of the chiral stationary phases based on natural and regenerated chitins

Mei

Chen

Bai

2017

J of Separation Science

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Natural and regenerated chitins were derivatized with 3,5-dimethyphenyl isocyanate. The corresponding chiral stationary phases were prepared by coating the resulting chitin derivatives on 3-aminopropyl silica gel. The swelling capacity of the chitin derivatives, enantioseparation capability, as well as eluents tolerance of the chiral stationary phases were evaluated. The results demonstrated no remarkable difference in enantioseparation capability between natural and regenerated chitins based chiral stationary phases. The similar enantioseparation characteristics of two chiral stationary phases could be understood by comparing the IR spectra of related chitin derivatives. The one of the two chiral stationary phases prepared by coating the chitin derivative with a lower molecular weight generally provided better enantioseparations. All chiral stationary phases can work in 100% chloroform, 100% ethyl acetate, 100% acetone, and the mobile phases containing a certain amount of tetrahydrofuran. The chiral stationary phase prepared from the chitin derivative with the highest swelling capacity exhibited better enantioseparations than others. This chiral stationary phase was damaged by flushing with 100% tetrahydrofuran, however, the enantioseparation capability was recovered again after the column was allowed to stand for 1 month. Furthermore, the recovered chiral stationary phase provided better enantioseparations for some chiral analytes than before.

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“…Polysaccharide-based CSPs include polysaccharide derivatives CSPs (such as ChiralCel OJ, OA, OB, OK, CA-1), cellulose carbamate derivatives (such as ChiralCel OD, OC, OG, OF) and amylose CSPs (such as ChiralPak AD, AS) [49] , [50] . Polysaccharide-based CSPs can be divided into coated and immobilized columns, which may exhibit different selectivities, because the conformation of the polymer is influenced by how the stationary phase is attached to the packing material [51] .…”

Section: Stereoselective Analytical Methodsmentioning

confidence: 99%

Significance and challenges of stereoselectivity assessing methods in drug metabolism

Shen

Zeng

2016

Journal of Pharmaceutical Analysis

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Stereoselectivity in drug metabolism can not only influence the pharmacological activities, tolerability, safety, and bioavailability of drugs directly, but also cause different kinds of drug–drug interactions. Thus, assessing stereoselectivity in drug metabolism is of great significance for pharmaceutical research and development (R&D) and rational use in clinic. Although there are various methods available for assessing stereoselectivity in drug metabolism, many of them have shortcomings. The indirect method of chromatographic methods can only be applicable to specific samples with functional groups to be derivatized or form complex with a chiral selector, while the direct method achieved by chiral stationary phases (CSPs) is expensive. As a detector of chromatographic methods, mass spectrometry (MS) is highly sensitive and specific, whereas the matrix interference is still a challenge to overcome. In addition, the use of nuclear magnetic resonance (NMR) and immunoassay in chiral analysis are worth noting. This review presents several typical examples of drug stereoselective metabolism and provides a literature-based evaluation on current chiral analytical techniques to show the significance and challenges of stereoselectivity assessing methods in drug metabolism.

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Insights into chromatographic enantiomeric separation of allenes on cellulose carbamate stationary phase

Cited by 29 publications

References 30 publications

Chiral Stationary Phases and their Relationship with Enantiomer Structures in Enantioseparation Research of Analytical Laboratory

Chiral Stationary Phases and their Relationship with Enantiomer Structures in Enantioseparation Research of Analytical Laboratory

Enantioseparation characteristics of the chiral stationary phases based on natural and regenerated chitins

Significance and challenges of stereoselectivity assessing methods in drug metabolism

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