Enantioseparation of DPP-4 Inhibitors on Immobilized Crown Ether-Based Chiral Stationary Phase

Gunnam, Srinivasu; Kandukuri, Nagesh Kumar; Ramachandra, Bondigalla; Choppari, Thirupathi; Chennuru, Lakshmi Narayana; Cherla, Parameswara Murthy

doi:10.1007/s10337-018-3626-x

Cited by 5 publications

(3 citation statements)

References 5 publications

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“…Materials and Methods. Table 3 shows the retention times of unsubstituted aniline (2) and certain substituted anilines (3)(4)(5)(6)(7)(8), (12)(13)(14) under 20 mM neutral phosphate buffer (pH 7.6). Figure 5 shows the retention pattern of substituted aniline isomers and 2-substituted anilines, which exhibited a higher or roughly the same retention in comparison with other isomers.…”

Section: Resultsmentioning

confidence: 99%

“…In this report, we show the selectivity of a crown ether type CSP, CROWNPAK CR-I (CR-I, Scheme 1 ), for isomeric substituted anilines and the related compounds. This type of CSP is known to have a higher chiral recognition ability for enantiomers having a primary amino group and to be particularly useful for the enantioseparation of natural and non-natural amino acids [ 6 , 7 , 8 , 9 ]. The chiral recognition of chiral crown ethers was developed by Cram et al [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

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Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

et al. 2021

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To understand the selectivity of the crown ether type chiral stationary phase (CSP), the retention selectivity for aniline and the positional isomers of substituted anilines were studied. In various substituted isomers, except nitroaniline, a remarkable decrease of retention due to steric hindrance was observed for the 2-substituted isomer. To determine the detailed molecular recognition mechanism, quantum chemical calculations were performed for the aggregates between the crown ether and the anilines. The results suggested that the 20-Crown-6, which includes a phenyl-substituted 1,1′-binaphthyl moiety, interacts with alkyl and aryl amines in an unconventional form different from the proposed one for 18-Crown-6.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

et al. 2021

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“…For the investigated amino acids, Br-substituted CSP had the highest chiral recognition ability and it provided a better resolution than the commercially available CSP. For the development and study of the direct enantiomeric separation of alogliptin, linagliptin, and saxagliptin, CROWNPAK CR-I (+) CSP was selected regarding the free amino group content of the investigated dipeptidyl peptidase-4 inhibitors [ 39 ]. Method optimization was performed by studying the effects of the solvent, additive, pH, and column temperature.…”

Section: Recent Applications Of Crown Ether-based Cspsmentioning

confidence: 99%

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

et al. 2021

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Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

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Chiral Materials: Progress, Applications, and Prospects

Niu

Zhao

Yan

et al. 2023

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Chirality is a universal phenomenon in molecular and biological systems, denoting an asymmetric configurational property where an object cannot be superimposed onto its mirror image by any kind of translation or rotation, which is ubiquitous on the scale from neutrinos to spiral galaxies. Chirality plays a very important role in the life system. Many biological molecules in the life body show chirality, such as the “codebook” of the earth's biological diversity‐DNA, nucleic acid, etc. Intriguingly, living organisms hierarchically consist of homochiral building blocks, for example, l‐amino acids and d‐sugars with unknown reason. When molecules with chirality interact with these chiral factors, only one conformation favors the positive development of life, that is, the chiral host environment can only selectively interact with chiral molecules of one of the conformations. The differences in chiral interactions are often manifested by chiral recognition, mutual matching, and interactions with chiral molecules, which means that the stereoselectivity of chiral molecules can produce changes in pharmacodynamics and pathology. Here, the latest investigations are summarized including the construction and applications of chiral materials based on natural small molecules as chiral source, natural biomacromolecules as chiral sources, and the material synthesized by design as a chiral source.

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Enantioseparation of DPP-4 Inhibitors on Immobilized Crown Ether-Based Chiral Stationary Phase

Cited by 5 publications

References 5 publications

Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

Achiral Molecular Recognition of Substituted Aniline Position Isomers by Crown Ether Type Chiral Stationary Phase

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

Chiral Materials: Progress, Applications, and Prospects

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