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Enantiomeric Recognition and Separation by Chiral Nanoparticles

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Enantiomeric Recognition and Separation by Chiral Nanoparticles molecules Review Enantiomeric Recognition and Separation by Chiral Nanoparticles Ankur Gogoi 1,† , Nirmal Mazumder 2,†, Surajit Konwer 3, Harsh Ranawat 2 , Nai-Tzu Chen 4 and Guan-Yu Zhuo 4,5,* 1 Department of Physics, Jagannath Barooah College, Jorhat, Assam 785001, India; [email protected] 2 Department of Biophysics, School of Life Sciences, Manipal Academy of Higher Education, Manipal, Karnataka 576104, India; [email protected] (N.M.); [email protected] (H.R.) 3 Department of Chemistry, Dibrugarh University, Dibrugarh, Assam 786004, India; [email protected] 4 Institute of New Drug Development, China Medical University, No. 91, Hsueh-Shih Rd., Taichung 40402, Taiwan; [email protected] 5 Integrative Stem Cell Center, China Medical University Hospital, No. 2, Yude Rd., Taichung 40447, Taiwan * Correspondence: [email protected]; Tel.: +886-4-2205-3366 (ext. 6508); Fax: +886-4-2207-1507 † These authors contributed equally to this work. Academic Editors: Maria Elizabeth Tiritan, Madalena Pinto and Carla Sofia Garcia Fernandes Received: 3 February 2019; Accepted: 10 March 2019; Published: 13 March 2019 Abstract: Chiral molecules are stereoselective with regard to specific biological functions. Enantiomers differ considerably in their physiological reactions with the human body. Safeguarding the quality and safety of drugs requires an efficient analytical platform by which to selectively probe chiral compounds to ensure the extraction of single enantiomers. Asymmetric synthesis is a mature approach to the production of single enantiomers; however, it is poorly suited to mass production and allows for only specific enantioselective reactions. Furthermore, it is too expensive and time-consuming for the evaluation of therapeutic drugs in the early stages of development. These limitations have prompted the development of surface-modified nanoparticles using amino acids, chiral organic ligands, or functional groups as chiral selectors applicable to a racemic mixture of chiral molecules. The fact that these combinations can be optimized in terms of sensitivity, specificity, and enantioselectivity makes them ideal for enantiomeric recognition and separation. In chiral resolution, molecules bond selectively to particle surfaces according to homochiral interactions, whereupon an enantiopure compound is extracted from the solution through a simple filtration process. In this review article, we discuss the fabrication of chiral nanoparticles and look at the ways their distinctive surface properties have been adopted in enantiomeric recognition and separation. Keywords: chirality; racemic mixture; enantiomer; enantiomeric recognition; enantiomeric separation; surface-modified nanoparticle; chiral ligand 1. Introduction Chirality is one of those fundamental properties of molecular systems which are ubiquitous in nature [1,2]. Notably, a number of important biological compounds including proteins, amino acids, nucleosides, sugars, and a number of hormones, which are the basic building blocks of life, are chiral and thus the chemistry of many fundamental biological (metabolic and regulatory) processes are directly controlled by such molecular systems [3,4]. Interestingly, enantiomers are mirror images of a chiral compound, e.g., chiral drugs, pesticides, herbicides, etc., which often exhibit profoundly different metabolic, pharmacological, therapeutic and/or toxicological properties [5]. Consequently, the two enantiomers of a chiral compound will react differently with the complementary receptor or Molecules 2019, 24, 1007; doi:10.3390/molecules24061007 www.mdpi.com/journal/molecules Molecules 2019, 24, 1007 2 of 31 Molecules 2019, 24, x 2 of 32 enzyme molecule in a biological environment which is highly stereoselective or enantioselective [6]. Consequently, the two enantiomers of a chiral compound will react differently with the Thiscomplementary issue is particularly receptor important or enzyme for themolecule pharmaceutical in a biological industry environment where many which drugs is highly currently in usestereoselective are known toor beenantioselective chiral (about [6]. 56%) This [ 4issue] out is of particularly which only important about 25% for the are pharmaceutical pure enantiomers. Besides,industry chirality where is alsomany important drugs currently for other in use industries are known like to agrochemical,be chiral (about food, 56%) petroleum,[4] out of which etc. [7–9]. For example,only about approximately 25% are pure 30–40%enantiomers. of the Besides, currently chir registeredality is also pesticides,important for insecticides other industries and herbicides like are chiralagrochemical,[6,8,10]. food, Most petroleum, of these currently etc. [7–9]. usedFor example, chiral compounds approximately are 30–40% racemates of the or mixturescurrently [11]. Importantly,registered while pesticides, one enantiomerinsecticides and of aherbicides chiral drug are chiral or agrochemical [6,8,10]. Most productof these currently has desired used effect (eutomer),chiral thecompounds other may are beracemates inactive or and/or mixtures cause [11]. adverse Importantly, side effects while inone many enantiomer cases(distomer) of a chiral [3,6]. drug or agrochemical product has desired effect (eutomer), the other may be inactive and/or cause Given the tremendous importance of chirality in many biochemical processes, recent years adverse side effects in many cases (distomer) [3,6]. witnessed enormous efforts among the researchers and manufacturing industries to prepare Given the tremendous importance of chirality in many biochemical processes, recent years enantiopurewitnessed compounds enormous efforts so that among an administeredthe researchers chiraland manufacturing compound (drugindustries or otherto prepare chemical compounds)enantiopure fits compounds properly to so the that target an bindingadministered site orchiral receptor compound molecule. (drug In or this other regard, chemical the ideal solutioncompounds) would be fits the properly enantioselective to the target synthesis binding site of justor receptor one of molecule. the enantiomers In this regard, (synthetic the ideal or chiral approachsolution [9, 12would,13]) be by the using enantioselective methods like synthesis isolation of ofjust natural one of compoundsthe enantiomers [14 ,(synthetic15], fermentation or chiral [16], asymmetricapproach synthesis [9,12,13]) [by17 ],using etc. methods Notably, like the isolation Nobel Prizeof natural in Chemistry compounds for [14,15], 2001 fermentation was awarded [16], for the developmentasymmetric of catalyticsynthesis asymmetric[17], etc. Notably, synthesis the Nobe withl Prize one halfin Chemistry jointly to for Knowles 2001 was and awarded Noyori for “for the their workdevelopment on chirally catalyzedof catalytic hydrogenation asymmetric synthesis reactions” with and one thehalf other jointly half to toKnowles Sharpless and “forNoyori his “for work on their work on chirally catalyzed hydrogenation reactions” and the other half to Sharpless “for his chirally catalyzed oxidation reactions” [18]. Unfortunately very few enantiopure compounds can be work on chirally catalyzed oxidation reactions” [18]. Unfortunately very few enantiopure obtained from natural sources. On the other hand, the use of asymmetric synthesis is limited due to compounds can be obtained from natural sources. On the other hand, the use of asymmetric the highsynthesis catalyst is limited cost and due time-consuming to the high catalyst synthesis cost and procedure,time-consuming albeit synthesis it is one procedure, of the most albeit powerful it methodsis one to of produce the most 100% powerful enantiopure methods to compounds produce 100% [12 enantiopure,19,20]. compounds [12,19,20]. As comparedAs compared to chiralto chiral approach, approach, the the racemicracemic approachapproach involves involves recognition recognition of racemates of racemates or or mixturesmixtures and subsequentand subsequent separation separation of the of enantiomers,the enantiomers, which which is relatively is relatively cost-effective cost-effective and and presents lowerpresents level of lower difficulty level [of20 difficulty]. This approach [20]. This isapproach based on is abased three-point on a three-point interaction interaction between between the analyte and athe chiral analyte selector and [ 12a ,21chiral–23 ].selector Briefly, [12,21–23]. a matched pairBriefly, undergoes a matched a three-point pair undergoes interaction a three-point whereas only one orinteraction two point whereas interaction only takesone or place two point in case interaction of a mismatched takes place pair, in case as shown of a mismatched in Figure1 .pair, A number as shown in Figure 1. A number of chiral selectors, including proteins, cyclodextrin (CD), crown ethers, of chiral selectors, including proteins, cyclodextrin (CD), crown ethers, oligo- and polysaccharides, etc., oligo- and polysaccharides, etc., have been developed till date. Unfortunately there is no universal have been developed till date. Unfortunately there is no universal chiral selector that can be efficiently chiral selector that can be efficiently applied for the recognition and/or separation of all types of appliedchiral for compounds the recognition [24]. and/or separation of all types of chiral compounds [24]. FigureFigure 1. Three-point1. Three-point interactioninteraction model model for fordescribing describing the homochiral the homochiral (true) and (true) heterochiral and heterochiral
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