Enantioseparation and selective detection of D-amino acids by ultra-high-performance liquid chromatography/mass spectrometry in analysis of complex biological samples

Müller, Constanze; Fonseca, Juliano; Rock, Theresa M.; Krauss‐Etschmann, Susanne; Schmitt‐Kopplin, Philippe

doi:10.1016/j.chroma.2013.11.026

Cited by 51 publications

(25 citation statements)

References 23 publications

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“…Muller at al. also reported the use of an UHPLC method based on derivatization to improve selectivity in the determination of D-amino acid in serum, plasma, and urine [19]. Specific derivatizing agents (namely, (R)-N-(3-pyridylthiocarbamoyl)pyrrolidine-2-carboxylic acid and (S)-3-amino-1-(3-pyridylthiocarbamoyl)pyrrolidine) were developed by Nagao et al to improve the UHPLC-MS determination of chiral amines and carboxylic acids for chiral metabolomics identification [20].…”

Section: Enantioselective Uhplc By Indirect Approachmentioning

confidence: 99%

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Ciogli

Ismail

Mazzoccanti

et al. 2018

J of Separation Science

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The ever-increasing need for enantiomerically pure chiral compounds has greatly expanded the number of enantioselective separation methods available for the precise and accurate measurements of the enantiomeric purity. The introduction of chiral stationary phases for liquid chromatography in the last decades has revolutionized the routine methods to determine enantiomeric purity of chiral drugs, agrochemicals, fragrances, and in general of organic and organometallic compounds. In recent years, additional efforts have been placed on faster, enantioselective analytical methods capable to fulfill the high throughput requirements of modern screening procedures. Efforts in this field, capitalizing on improved chromatographic particle technology and dedicated instrumentation, have led to highly efficient separations that are routinely completed on the seconds time scale. An overview of the recent achievements in the field of ultra-high-resolution chromatography on column packed with chiral stationary phases, both based on sub-2 μm fully porous and sub-3 μm superficially porous particles, will be given, with an emphasis on very recent studies on ultrafast chiral separations.

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Section: Enantioselective Uhplc By Indirect Approachmentioning

confidence: 99%

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Ciogli

Ismail

Mazzoccanti

et al. 2018

J of Separation Science

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“…[7][8][9] However, the importance of D-amino acids has been highlighted by recent reports of their great influence on bacteria growth and biofilm formation. [10][11][12] Accordingly, in addition to recognition of D-amino acids via spectroscopic and chromatographic approach has been proposed. 13,14 The development of supramolecular chemistry has opened a new avenue for recognition of chiral compounds.…”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition of d-Tryptophan by Confining High-Energy Water Molecules Inside the Cavity of Copper-Modified β-Cyclodextrin

Tao¹,

Gu²,

Deng³

et al. 2015

J. Phys. Chem. C

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We report a Cu 2+ -modified β-cyclodextrin, Cu 2 -β-CD, that was self-assembled on poly(L-glutamic acid) (P-L-Glu) for chiral recognition of D-tryptophan (D-Trp). Cu 2+ formed binuclear hydroxy-bridge (Cu(OH) 2 Cu) at the wider opening of the cavity of β-CD and acted as a cap to prevent high-energy water molecules from being released while forcing Trp isomers to enter through its narrower opening. Because H-bonds were favored to form between the high-energy water molecules and the amino groups of D-Trp inside the cavity of β-CD, D-Trp was thus recognized. The recognition capability of the Cu 2 -β-CD appeared to depend on the way the Cu 2 -β-CD self-assembled onto P-L-Glu, preferring via H-bonds rather than via electrostatic interactions, because electrostatic interactions between P-L-Glu and Cu(OH) 2 Cu could alter the configuration of the Cu 2 -β-CD cavity, resulting in weakened H-bonds between high-energy water molecules and D-Trp.

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“…After the addition of the precipitant, the samples should be mixed in all volumes. Until centrifugation, immersion in an ice bath can be used (Calderón-Santiago et al 2012 ; Harder et al 2011 ; Müller et al 2014 ). For better separation, tubes with membranes can be used during centrifugation.…”

Section: Sample Preparationmentioning

confidence: 99%

“…In most studies (Li et al 2011a , b ; Müller et al 2014 ; Sharma et al 2014 ; Song et al 2013 ; Voehringer et al 2013 ), the identification and quantitation of AAs in biological samples was performed by high-performance liquid chromatography (HPLC) analysis with fluorescence detection (FLD), after derivatization of compounds with o-phthalaldehyde/mercaptoethanol (OPA) and 2-mercaptoethanol (MCE). It should be noted that besides derivatization of primary AAs, amino esters, amino alcohols, alkyl-aryl amines, heterocyclic amines can be applied.…”

Section: Sample Preparationmentioning

confidence: 99%

“…Recent studies have shown that d -amino acids (D-AAs) are present in organisms at a higher level and to a greater extent than previously considered. D-AAs meet certain biological functions in the body (Müller et al 2014 ), and are considered as new bioactive compounds and biomarkers (Hammase et al 2009 ). Sato et al ( 2021 ) have provided research showing that L-type amino acid transporter 1 is associated with chemoresistance in breast cancer via the promotion of amino acid metabolism.…”

Section: Introductionmentioning

confidence: 99%

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Determination of amino acids in human biological fluids by high-performance liquid chromatography: critical review

2021

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The quantitation and qualification of amino acids are most commonly used in clinical and epidemiological studies, and provide an excellent way of monitoring compounds in human fluids which have not been monitored previously, to prevent some diseases. Because of this, it is not surprising that scientific interest in evaluating these compounds has resurfaced in recent years and has precipitated the development of a multitude of new analytical techniques. This review considers recent developments in HPLC analytics on the basis of publications from the last few years. It helps to update and systematize knowledge in this area. Particular attention is paid to the progress of analytical methods, pointing out the advantages and drawbacks of the various techniques used for the preparation, separation and determination of amino acids. Depending on the type of sample, the preparation conditions for HPLC analysis change. For this reason, the review has focused on three types of samples, namely urine, blood and cerebrospinal fluid. Despite time-consuming sample preparation before HPLC analysis, an additional derivatization technique should be used, depending on the detection technique used. There are proposals for columns that are specially modified for amino acid separation without derivatization, but the limit of detection of the substance is less beneficial. In view of the fact that amino acid analyses have been performed for years and new solutions may generate increased costs, it may turn out that older proposals are much more advantageous.

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Enantioseparation and selective detection of D-amino acids by ultra-high-performance liquid chromatography/mass spectrometry in analysis of complex biological samples

Cited by 51 publications

References 23 publications

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Enantioselective ultra high performance liquid and supercritical fluid chromatography: The race to the shortest chromatogram

Chiral Recognition of d-Tryptophan by Confining High-Energy Water Molecules Inside the Cavity of Copper-Modified β-Cyclodextrin

Determination of amino acids in human biological fluids by high-performance liquid chromatography: critical review

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