Simultaneous determination of mandelic acid enantiomers and phenylglyoxylic acid in urine by high-performance liquid chromatography with precolumn derivatization

Wang, Jinzhao; Wang, Xiangjun; Tang, Yanhui; Shen, Shuijie; Jin, Yin-Xiu; Zeng, Su

doi:10.1016/j.jchromb.2006.04.037

Cited by 18 publications

(12 citation statements)

References 8 publications

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“…The observed enantioselectivities do not correlate both with electronic properties (Hammet sigmas) or acidity (pK a ) of mandelic acids, suggesting that sterically driven parameters or hydrogen bonding/dipoledipole interaction are likely to be responsible for chiral discrimination. Interestingly, the methylation of the hydroxyl group of 4-trifluoromethylmandelic acid (20) led to a pronounced decrease of enantioselectivity which might be attributed to the change of hydrogen bonding/donating capacity.…”

Section: Chromatographymentioning

confidence: 99%

“…They also found application in medicinal, cosmetic, and agrochemical industry [17,18]. Enantioselective analytics of mandelic acid and their derivatives by HPLC is not very frequently reported [19][20][21][22][23]. Typically, methods of their enantioseparation involve ligand-exchange or chiral additive approaches and most of them suffer from a need of derivatization, low selectivity, or long analysis times [22].…”

Section: Introductionmentioning

confidence: 99%

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Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Kacprzak

Maier

Lindner

2010

J of Separation Science

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Replacement of the flexible thioether linker for the novel, rigid 1,2,3-triazole spacer group in the course of immobilization of quinine tert-butyl carbamate onto a silica surface led to a chiral stationary phase (CSP) with enhanced enantioselectivity for the resolution of mandelic acid and derivatives thereof. These new CSPs allowed efficient resolution of a wide set of mandelic acids with α-values between 1.08 and 1.68. The high loadability of these chiral ion exchange type CSPs allows preparative separation in the milligram range on an analytical column of 100×4 mm id in a single run as it was demonstrated for 4-trifluoromethylmandelic, 2-naphthylglycolic and 3,4-methylenedioxymandelic acids. The chiral recognition process has been studied using a library of 25 diverse racemic probes. A tentative model suggests that the rigid 1,2,3-triazole group takes part in the formation of an enantioselective-binding pocket of the entire and immobilized selector moiety of the CSP. The primary interaction site is given by the ionizable quinuclidine group of the Cinchona alkaloid supported by possible π-π stabilization effects within the selector-selectand complex.

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Section: Chromatographymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Kacprzak

Maier

Lindner

2010

J of Separation Science

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“…Mandelic acid (MA) is one of the major mammal urinary metabolites of styrene [1,2], a hazardous pollutant widely used as a monomer in plastic industry [3]. e toxicity of styrene is metabolism-dependent [4] and stems from its bioactivation to styrene oxide, which in turn generates a cascade of metabolites including MA [1].…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis of (±)‐Mandelic Acid‐d₅, Optical Resolution, and Absolute Configuration Determination

Bruno

Lentini

Lovece

et al. 2012

Journal of Chemistry

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An efficient microwave-assisted synthesis of(±)-mandelic acid-d5was developed. The racemic mixture was resolved by diastereomeric salt formation using 1-phenylethylamine enantiomers as resolving agents. At each step, the resolution process was checked by determining mandelic acid-d5enantiomer ee values directly on fractional crystallized diastereomeric salts by chiral capillary electrophoresis analysis. Highly enriched (−)- and (+)-mandelic acid-d5(95% and 90% ee, resp.) were obtained and their absolute configurations—RandS, respectively—were determined by correlation of the (−)-mandelic acid-d5circular dichroism spectrum to the (R)-mandelic acid one.

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“…Mandelic acid (MA, structure of its two enantiomers see Fig. 1) is one of the major urinary metabolites of styrene in both rodents and humans 4, 5. It can be further metabolized to phenylglyoxylic acid (PGA).…”

Section: Introductionmentioning

confidence: 99%

Study on the metabolic mechanism of chiral inversion of S‐Mandelic acid in vitro

et al. 2011

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Mandelic acid (MA) is generally used as a biological indicator of occupational exposure to styrene, which is classified as a class of hazardous environmental pollutants. It was found to undergo one-directional chiral inversion (S-MA to R-MA) in Wistar and Sprague-Dawley rats in vivo. This study was aimed to explore the metabolic mechanism of chiral inversion of S-MA in vitro. S-MA was converted to R-MA in rat hepatocytes, whereas MA enantiomers remained unchanged in acidic and neutral phosphate buffers, HepG2 cells, and intestinal flora. In addition, the synthesized S-MA-CoA thioester was rapidly racemized and hydrolyzed to R-MA by rat liver homogenate and S9, cytosolic and mitochondrial fractions. The data suggest that chiral inversion of S-MA may involve the hydrolysis of S-MA-CoA, and its metabolic mechanism could be the same as that of 2-arylpropionic acid (2-APA) drugs.

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Simultaneous determination of mandelic acid enantiomers and phenylglyoxylic acid in urine by high-performance liquid chromatography with precolumn derivatization

Cited by 18 publications

References 8 publications

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Microwave‐Assisted Synthesis of (±)‐Mandelic Acid‐d₅, Optical Resolution, and Absolute Configuration Determination

Study on the metabolic mechanism of chiral inversion of S‐Mandelic acid in vitro

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Simultaneous determination of mandelic acid enantiomers and phenylglyoxylic acid in urine by high-performance liquid chromatography with precolumn derivatization

Cited by 18 publications

References 8 publications

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Unexpected enantioseparation of mandelic acids and their derivatives on 1,2,3‐triazolo‐linked quinine tert‐butyl carbamate anion exchange‐type chiral stationary phase

Microwave‐Assisted Synthesis of (±)‐Mandelic Acid‐d5, Optical Resolution, and Absolute Configuration Determination

Study on the metabolic mechanism of chiral inversion of S‐Mandelic acid in vitro

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Microwave‐Assisted Synthesis of (±)‐Mandelic Acid‐d₅, Optical Resolution, and Absolute Configuration Determination