Cysteine-based chiral selectors for the ligand-exchange separation of amino acids☆

Natalini, Benedetto; Sardella, Roccaldo; Macchiarulo, Antonio; Pellicciari, Roberto

doi:10.1016/j.jchromb.2008.06.007

Cited by 30 publications

(19 citation statements)

References 40 publications

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“…separated or nonseparated racemates, can be easily individuated. This concept has been recently adapted by Natalini et al [148,149] that carried out a descriptive structure-separation relationship (DSSR) in which some set of physicochemical descriptors are directly used with a partition tree or a classification model towards the experimental enantioselectivities. In a quantitative form also Del Rio and Gasteiger [147] applied this idea to devise a simple method based on the atomic counts around the chiral centre to assess whether a compound will be separated or not on a Whelk-O1 CSP.…”

Section: Discussionmentioning

confidence: 99%

Exploring enantioselective molecular recognition mechanisms with chemoinformatic techniques

Río

2009

J of Separation Science

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A comprehensive review of chemoinformatic techniques and studies applied to the field of enantioselective molecular recognition is presented. Several approaches such as enantiophores/pharmacophore modelling, QSPRs, CoMFA and other insightful data mining procedures are discussed. The review focuses on the central role of chemoinformatic approaches on the establishment of connections between available experimental data, mainly HPLC separation data, and these algorithms that describe properties of chiral molecules. The general overview of the aforementioned calculations account for a use of these techniques as a valuable strategy to achieve reliable prediction systems, infer the mechanisms of chiral recognition, generate insight for the conception of new chiral receptors and corroborate and assist experimental techniques such as chiral LC. Moreover, it is pointed out that computer methods in this field promise a wide range of applications for both academia and industry, ranging from enantioselective reactions, drug discovery and analysis of high-throughput screenings, to analytical and semi-preparative separations or large-scale production of enantiopure compounds.

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Section: Discussionmentioning

confidence: 99%

Exploring enantioselective molecular recognition mechanisms with chemoinformatic techniques

Río

2009

J of Separation Science

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“…Cu(II) is the chelating metal ion of first choice, while Zn(II) and Ni(II) may be proper alternatives [3]. Frequently employed CLEC type selectors include cyclic amino acids such as proline [4] and hydroxyproline [5] as well as sulfur containing amino acids derived from cysteine [6] and penicillamine [7], and also amino alcohols [8].…”

Section: Introductionmentioning

confidence: 99%

Chiral ligand-exchange chromatography with Cinchona alkaloids. Exploring experimental conditions for enantioseparation of α-amino acids

Echevarria

Franca

Tascón

et al. 2016

Microchemical Journal

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“…Among these, it is worth mentioning the amino acids proline, hydroxyproline (Davankov and Kurganov, 1983;Yamskov et al, 1981), cysteine (Natalini et al, , 2008b(Natalini et al, , 2008c, histidine Watanabe, 1983), phenylalanine (Wan et al, 1997;Wernicke, 1995), alanine (Tsvetkov and Mingelgrin, 1987), lysine (Tsvetkov and Mingelgrin, 1987), isoleucine (Huang et al, 2005), and penicillamine (Ôi et al, 1995), and few amino alcohols carrying a phenylglycinol (Hyun et al, 2003(Hyun et al, , 2004, leucinol (Hyun and Ryoo, 1996;Hyun et al, 2002), or pyrrolidinemethanol (Natalini et al, 2007) residual as the basic scaffold.…”

Section: Introductionmentioning

confidence: 99%

“…In this setting, we developed three C-CSPs based on the cysteine derivatives S-benzyl-(R)-cysteine ((R)-SBC) (Figure 1(a)) , S-diphenylmethyl-(R)-cysteine ((R)-SDC) (Figure 1(b)) (Natalini et al, 2008b), and S-trityl-(R)-cysteine ((R)-STC) (Figure 1(c)) (Natalini et al, 2008c), which were physically adsorbed onto a conventional octadecylsilica carpet. The three derived enantiorecognition materials were very effective towards the enantioseparation of a large number of a-amino acids.…”

Section: Introductionmentioning

confidence: 99%

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

Sardella

Ianni

Lisanti

et al. 2015

Critical Reviews in Analytical Chemistry

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The stratification of 0.040-0.050 g of S-trityl-(R)-cysteine ((R)-STC) onto a conventional ODS phase produces a very effective (α and RS up to 5.71 and 12.09, respectively) and stable (more than 30 days of repeated analysis) chiral ligand-exchange chromatography (CLEC) coated chiral stationary phase (C-CSP). With a few specific exceptions, a (R) < (S) enantiomer elution order can be easily predicted. The (R)-STC-based C-CSP can be successfully exploited also at a preparative level for enantioisolations of CNS active amino acids (AAs), with a racemate loadability up to 0.015 g for single injection. The CLEC (R)-STC-based system can be helpful in monitoring the presence of (R)-AAs in edible products and other organic materials, thus contributing to evaluating product quality and diagnosing subclinical pathological states in animals and humans. Very profitably, molecular modeling-based computer-assisted classification analyses can reveal the actual enantioseparation ability of the (R)-STC phase towards a specific compound.

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Cysteine-based chiral selectors for the ligand-exchange separation of amino acids☆

Cited by 30 publications

References 40 publications

Exploring enantioselective molecular recognition mechanisms with chemoinformatic techniques

Exploring enantioselective molecular recognition mechanisms with chemoinformatic techniques

Chiral ligand-exchange chromatography with Cinchona alkaloids. Exploring experimental conditions for enantioseparation of α-amino acids

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

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