Enantiomeric separation of ornithine in complex mixtures of amino acids by EKC with off-line derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate

Martínez‐Girón, Ana Belén; Domínguez‐Vega, Elena; García-Ruiz, Carmen; Crego, Antonio L.; Marina, Marı́a Luisa

doi:10.1016/j.jchromb.2008.06.022

Cited by 24 publications

(15 citation statements)

References 34 publications

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“…Orn Isomers. Martínez-Giró n et al [113] [192] developed analytical methods for the separation of unnatural ornithine isomers that may be present in processed foods.…”

Section: 4mentioning

confidence: 99%

Origin, Microbiology, Nutrition, and Pharmacology of D‐Amino Acids

Friedman

2010

Chemistry & Biodiversity

162

108

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Exposure of food proteins to certain processing conditions induces two major chemical changes: racemization of all L-amino acids (LAAs) to D-amino acids (DAAs) and concurrent formation of cross-linked amino acids such as lysinoalanine (LAL). The diet contains both processing-induced and naturally-formed DAA. The latter include those found in microorganisms, plants, and marine invertebrates. Racemization impairs digestibility and nutritional quality. Racemization of LAA residues to their D-isomers in food and other proteins is pH-, time-, and temperature-dependent. Although racemization rates of LAA residues in a protein vary, relative rates in different proteins are similar. The nutritional utilization of different DAAs varies widely in animals and humans. Some DAAs may exert both adverse and beneficial biological effects. Thus, although D-Phe is utilized as a nutritional source of L-Phe, high concentrations of D-Tyr in such diets inhibit the growth of mice. Both D-Ser and LAL induce histological changes in the rat kidney. The wide variation in the utilization of DAAs is illustrated by the fact that, whereas D-Meth is largely utilized as a nutritional source of the L-isomer, D-Lys is not. Similarly, although L-CysSH has a sparing effect on L-Meth when fed to mice, D-CysSH does not. Since DAAs are consumed as part of their normal diet, a need exists to develop a better understanding of their roles in foods, microbiology, nutrition, and medicine. To contribute to this effort, this overview surveys our present knowledge of the chemistry, nutrition, safety, microbiology, and pharmacology of DAAs. Also covered are the origin and distribution of DAAs in food and possible roles of DAAs in human physiology, aging, and the etiology and therapy of human diseases.

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“…Orn Isomers. Martínez-Giró n et al [113] [192] developed analytical methods for the separation of unnatural ornithine isomers that may be present in processed foods.…”

Section: 4mentioning

confidence: 99%

Origin, Microbiology, Nutrition, and Pharmacology of D‐Amino Acids

Friedman

2010

Chemistry & Biodiversity

162

108

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“…Thus, several works have reported the enantiomeric separation of Orn by CE [15][16][17][18][19]. Some of them have been developed in our research group, reaching analysis times lower than 15 min, even showing their potential in food analysis [17][18][19]. However, the use of UV detection in these works originated limitations in the analysis of complex matrices.…”

Section: Introductionmentioning

confidence: 99%

Development of a CE‐ESI‐ITMS method for the enantiomeric determination of the non‐protein amino acid ornithine

et al. 2009

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Unequivocal enantiomeric determination by CE-MS2 of the non-protein amino acid ornithine (Orn), previously derivatized with FITC, was carried out in this work. A CE-tandem MS system was used to combine the potential of CE in chiral separations with the sensitivity and selectivity of tandem MS detection. The electrospray-coaxial sheath flow interface conditions were optimized and an IT analyzer working in the MS2 mode was employed to provide the best sensitivity and selectivity. Satisfactory results were obtained in terms of linearity (r2 > 0.99), precision (RSD from 1.3 to 2.3% for migration times and from 11.0 to 18.6% for corrected peak areas), and LOD (2 x 10(-9) M). Interestingly, the CE-MS2 method developed allowed a sensitivity enhancement of 100 folds with respect to UV detection. The results demonstrated the feasibility for carrying out quantitative CE-ESI-MS2 determinations of Orn enantiomers in beers. Thus, L-Orn was found in the 16 beer samples analyzed at concentrations ranging from 1 x 10(-6) to 2 x 10(-5) M, whereas the percentages of D-Orn with respect to the total amount of Orn reached values between 1.5 and 10.0%.

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“…A CE method in the EKC separation mode using HS-b-CD and Ac-g-CD as chiral selectors in acidic media has recently been developed by our research team for the chiral separation of amino acids [31]. This method demonstrated a huge enantiomeric separation potential for chiral protein amino acids including Arg and Lys, and the chiral nonprotein amino acid Orn.…”

Section: Development Of the In-capillary Derivatization Methods By Cementioning

confidence: 99%

“…In addition, a previous CE separation method using pre-capillary derivatization with AQC has demonstrated a huge separation potential for amino acids enantiomers [31].…”

Section: Introductionmentioning

confidence: 99%

Development of an in‐capillary derivatization method by CE for the determination of chiral amino acids in dietary supplements and wines

et al. 2009

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A fast in-capillary derivatization method by CE with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate was developed for the first time for the determination of amino acid enantiomers (arginine, lysine, and ornithine) in dietary supplements and wines. Because of the initial current problems due to the formation of precipitates into the capillary during the derivatization reaction, a washing step with an organic solvent as DMSO between injections was necessary. Different approaches were also investigated to enhance the sensitivity of detection. A derivatization procedure, where plugs of ACN, derivatizing agent (10 mM 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate), and sample in borate (1:1 v/v) were injected in tandem (2, 3, and 6 s, respectively, at 50 mbar), was selected because it enabled to obtain the most sensitive and reproducible results. Appropriate analytical characteristics (linearity, LOD and LOQ, precision, absence of matrix interferences, and accuracy) were obtained for this method. Finally, the optimized method was successfully applied to the determination of the enantiomers of arginine, lysine, and ornithine in food samples of different complexities (dietary supplements and wines).

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Enantiomeric separation of ornithine in complex mixtures of amino acids by EKC with off-line derivatization with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate

Cited by 24 publications

References 34 publications

Origin, Microbiology, Nutrition, and Pharmacology of D‐Amino Acids

Origin, Microbiology, Nutrition, and Pharmacology of D‐Amino Acids

Development of a CE‐ESI‐ITMS method for the enantiomeric determination of the non‐protein amino acid ornithine

Development of an in‐capillary derivatization method by CE for the determination of chiral amino acids in dietary supplements and wines

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