β-cyclodextrin modified silica nanochannel membrane for chiral separation

Liu, Yue; Li, Ping; Li, Jingchi; Fan, Dingyan; Huang, Shasheng

doi:10.1016/j.memsci.2013.10.064

Cited by 37 publications

(15 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chiral compounds, especially chiral drugs, have identical physical and chemical properties but very often exhibit different biological, pharmacological, toxicological activities, and metabolism pathways in living system. Diverse analytical techniques have been developed for separating chiral compounds including various chromatography, CE , membrane separation, crystallization, metal organic framework, and chemical recognition . However, most techniques require time‐consuming procedures, high cost, quite large consumption of solvents, as well as complicated pre‐treatment steps for samples.…”

Section: Methodsmentioning

confidence: 99%

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Kim

Lee

2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Chirality is a universal and important phenomenon in nature. It refers to the property of a molecule or system which is not identical to its mirror image. In chemical field, chirality is used to describe the lack of a symmetric plane in molecules. Chiral compounds, especially chiral drugs, have identical physical and chemical properties but very often exhibit different biological, pharmacological, toxicological activities, and metabolism pathways in living system. Diverse analytical techniques have been developed for separating chiral compounds including various chromatography, 1-5 CE, 6 membrane separation, 7,8 crystallization 9 , metal organic framework, 10 and chemical recognition. 11 However, most techniques require time-consuming procedures, high cost, quite large consumption of solvents, as well as complicated pre-treatment steps for samples. Thus, it leads to an increasing demand for developing simple and efficient methods for chiral separation.Cyclodextrin and their derivatives, such as carboxymethylβ-cyclodextrin (CMCD), which consist of a hydrophobic internal cavity and a hydrophilic outer surface have been used widely as a chiral selector because of their excellent chiral recognition capabilities. [12][13][14] In this study, we report the synthesis of carboxymethyl-β-cyclodextrin modified zirconiapoly(amidoamine) (PAMAM) dendrimer-magnetic microspheres (CMCD-ZPMMs) that was carried out via repetitive Michael addition reactions by using microwave irradiation. The product was tried to apply in selective enantioseparation of racemic drugs using polarimetric technique. To the best of our knowledge, the direct separation of racemic drugs by using CMCD-ZPMMs has not been reported yet.The scheme of the preparation for CMCD-ZPMMs is displayed in Scheme 1. Firstly, magnetic microspheres, Fe 3 O 4 were synthesized via solvothermal reaction, and then coated with glucose by hydrothermal reaction before coating with zirconia. The surface of Zirconia magnetic microspheres was modified with (3-aminopropyl) triethoxysilane (APTES) to form primary amine groups. The morphologies of obtained products were investigated in our previous report. 15 Subsequently, to make more bonding sites for efficient conjugation with chiral selector, PAMAM dendrimers were grown onto ZPMMs by repeating the Michael addition and amidation reaction by using ultrasonic system. The synthetic procedures for preparing CMCD-ZPMMs are presented in Supporting information (Appendix S1).Initial assessments of CMCD-ZPMMs for separating chiral drugs were performed using ketopropen, propranolol, and acebutolol. Sample solutions containing these three drugs showed no optical activity because they are comprised of equal amounts of the (+) and (−) enantiomers, called a racemic mixture. It is well-known that the sign (+/−) of the rotation change depends on the nature and macroscopic behavior of the compound, such as the substituents attached to the stereocenter, the number of molecules in the path of the light. The scheme of the separation of racemic drugs vi...

show abstract

Section: Methodsmentioning

confidence: 99%

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Kim

Lee

2016

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

show abstract

“…Apart from the above‐mentioned enantiomeric detection strategies, various other conjugated CD‐NPs can be used for enantioseparation, whereby the properties of the NP are exploited to aid in the separation process after formation of complexes with chiral analytes (Table ). One such method utilises the novel nanomaterial to interact and complex with one of the chiral forms of the analyte, allowing for a second step to physically separate complexed material and solution resulting in enantioseparation of analyte . The novel nanomaterial can also be employed within capillary electrophoresis for enantioseparation, whereby the CD bound material can be used as either a pseudostationary phase or within the running buffer, both methods allowing for effective separation of various chiral analytes.…”

Section: Cyclodextrin Functionalised Nanomaterials In Chiral Recognitionmentioning

confidence: 99%

Cyclodextrin‐Functionalised Nanomaterials for Enantiomeric Recognition

Hobbs

Řezanka

2020

ChemPlusChem

View full text Add to dashboard Cite

which are glucose-based cyclic oligosaccharides, are materials that can act inherently as chiral selectors, with many reports of the application of cyclodextrins in enantioseparation. However, many studies have encountered the problem of insufficient enantioselective performance of the chiral selector. One of the main reasons is due to low surface concertation's, whereby interaction between the chiral selector and analyte usually occurs at a surface. Thus, scientists have been trying for the last two decades to overcome this problem, with the incorporation of nanomaterials being promising as they possess a large surface area which allows for the accommodation of a higher concentration of the chiral selectors. Herein, we outline nanomaterial-cyclodextrin conjugates that work in tandem to achieve or enhance enantioselectivity through various methods such as chromatography, adsorption, and removal using magnetic nanoparticles, or enantiorecognition using electrochemical techniques.

show abstract

“…Polymers containing incorporated chiral selectors, such as beta-cyclodextrin [87][88][89][90], crown ether derivatives [91], bovine serum albumin [92], apoenzymes [93], antibodies [94], DNA [36,[94][95][96], and terpenes [97] were used to obtain membranes functionalized with immobilized chiral selectors. Different methods can be used for chiral selector immobilization on surface, in pores, or in bulk configuration on base membranes, including impregnation, covalent grafting, or esterification [26].…”

Section: Introductionmentioning

confidence: 99%

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

2017

View full text Add to dashboard Cite

Given the importance of chirality in the biological response, regulators, industries and researchers require chiral compounds in their enantiomeric pure form. Therefore, the approach to separate enantiomers in preparative scale needs to be fast, easy to operate, low cost and allow obtaining the enantiomers at high level of optical purity. A variety of methodologies to separate enantiomers in preparative scale is described, but most of them are expensive or with restricted applicability. However, the use of membranes have been pointed out as a promising methodology for scale-up enantiomeric separation due to the low energy consumption, continuous operability, variety of materials and supports, simplicity, eco-friendly and the possibility to be integrated into other separation processes. Different types of membranes (solid and liquid) have been developed and may provide applicability in multi-milligram and industrial scales. In this brief overview, the different types and chemical nature of membranes are described, showing their advantages and drawbacks. Recent applications of enantiomeric separations of pharmaceuticals, amines and amino acids were reported.

show abstract

β-cyclodextrin modified silica nanochannel membrane for chiral separation

Cited by 37 publications

References 19 publications

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Facile Synthesis and Enantioseparation of Chiral Drugs Using Zirconia Magnetic Microspheres Coated with Cyclodextrin/Poly(amidoamine) Dendrimers

Cyclodextrin‐Functionalised Nanomaterials for Enantiomeric Recognition

Chiral Separation in Preparative Scale: A Brief Overview of Membranes as Tools for Enantiomeric Separation

Contact Info

Product

Resources

About