Optical Resolution of Racemic α-Amino Acids on a Dynamic Chiral Stationary Phase Derived from (S)-Leucinol by Ligand Exchange Chromatography

Hyun, Myung Ho; Ryoo, Jae-Jeong

doi:10.1080/10826079608014044

Cited by 20 publications

(9 citation statements)

References 10 publications

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“…11,12 An interesting alternative was produced by introducing chiral alkyl groups onto the glycine nitrogen; in this case, there is no asymmetric carbon atom within the chelate ring, chirality being introduced with the Nsubstituent. [13][14][15][16] Following the observation that the presence of a phenyl ring in previously utilized selectors like N,N-dimethyl-(S)-phenylalanine (S-DMP) 17 and O-benzyl-(S)-serine (S-OBS) 18 results in a mixed, dynamically coated CSP, and with the aim to evaluate the influence of structural features on chiral differentiation and hence contribute to the understanding of the process and widen its scope, we have substituted the serine oxygen for a sulfur atom, thus affording S-benzyl-(R)-cysteine (R-SBC, Fig. 1), a new, rather inexpensive chiral selector endowed with a strong lipophilic character that comes through the combination of the sulfur atom and the aromatic ring.…”

Section: Introductionmentioning

confidence: 99%

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

et al. 2006

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S-benzyl-(R)-cysteine (R-SBC) is a new chiral ligand-exchange stationary phase which has proved to be effective in the analytical separation of some natural and unnatural underivatized amino acids with fair to good separation and resolution factors. The dynamic coating of the RP-18 solid support with S-Benzyl-(R)-cysteine (R-SBC) gives rise to a stable and efficient chiral stationary phase (CSP) that has been successfully employed. The mechanism of chiral recognition is discussed and a molecular modeling study aimed at identifying molecular descriptors responsible for observed different behaviours of analytes upon different albeit closely related selectors is discussed.

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Section: Introductionmentioning

confidence: 99%

Dynamic ligand‐exchange chiral stationary phase from S‐benzyl‐(R)‐cysteine

et al. 2006

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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%

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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“…Proline, hydroxyproline or other amino acids have been successfully utilized as chiral selectors for the preparation of ligand exchange CSPs [4][5][6][7]. Amino alcohol derivatives such as (S)-leucinol derivative, sodium N-[(S)-1-hydroxymethyl-3-methylbutyl]-Nundecylaminoacetate, and (R)-phenylglycinol derivative, sodium N-[(R)-2-hydroxy-1-phenylethyl]-N-undecylaminoacetate, covalently bonded to silica gel [10,11] or dynamically coated on octadecylsilica gel [12] were also quite successful as ligand exchange CSPs for the resolution of ␣-and ␤-amino acids and ␣-hydroxycarboxylic acids [10][11][12][13][14][15][16][17]. Especially, a CSP (CSP 1, Fig.…”

Section: Introductionmentioning

confidence: 99%