Determination of d-amino acids by deuterium labelling and selected ion monitoring

Liardon, R.; Ledermann, Simone; Ott, Ursula

doi:10.1016/s0021-9673(00)80309-x

Cited by 84 publications

(56 citation statements)

References 15 publications

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“…As it was already studied and widely discussed by several authors, (Liardon and Ledermann, 1981;Liardon and Hurrell, 1983;Bada, 1984) the hydrolytic treatment (6N HCL, at 110° C, for 24 h) applied in sample preparation induced racemization that should be taken into account in a reliable determination and discussion of results. Induced racemization quantity depends on the nature of both Bellagamba et al [Ital J Anim Sci vol.14:2015]…”

Section: Resultsmentioning

confidence: 99%

“…Five hundred mg of each sample were defatted by methanol-chloroform extraction (Bligh and Dyer, 1959) than 100 mg hydrolysed in 6N HCl, under vacuum, at 110°C for 24 h (Liardon and Ledermann, 1981). Hydrolysis of standard proteins was carried out on 5 mg. After hydrolysis, the hydrochloric acid was removed under vacuum on a rotary evaporator (Buchi R-210, Switzerland) and the dried residue was dissolved in 0.1 M HCl (2 mL) and filtered.…”

Section: Dl-amino Acid Purification and Separation Analysis By Reversmentioning

confidence: 99%

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The Impact of Processing on Amino Acid Racemization and Protein Quality in Processed Animal Proteins of Poultry Origin

Bellagamba

Caprino

Mentasti

et al. 2015

Italian Journal of Animal Science

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Re-authorization of processed animal proteins (PAPs) in EU, derived from by-products of human food production, could increase manufacturing of proteins for feed ingredients and reduce the need of imported proteins mainly of plant origin. The PAPs production is largely done by the rendering process during which authorized animal by-products are heat treated to extract valuable protein and animal fat, ensuring sterilizing conditions of raw incoming materials. Proteins exposure to certain processing conditions induces two important chemical changes, racemization of amino acids and formation of cross-linked amino acid. These changes are associated with appreciable reduction of protein digestibility and nutritional value. The aim of this study was to verify the effect of heat treatment on amino acid racemization in processed animal proteins of poultry origin and related nutritional implications by evaluation of their in vitro digestibility. The results reported confirm the detection of racemized amino acids in processed animal proteins, especially D-aspartic acid, as realistic indicators of thermal treatments during PAP manufacturing. In our results, the severe (115°C) and prolonged heat treatment (180 minutes) revealed a D-Asp content of 28.1%.Prolongation of temperature treatment (20, 30 and 180 min, at 115°C) significantly (P<0.05) affects in vitro protein digestibility, which decrease from 86.0%, in no-treated sample, to 78.3% and 79.1% after 20 and 30 min, respectively, and to 76.3% after 180 min. The processing conditions applied during PAPs preparations and the racemization of proteins amino acids may reasonably be involved in the loss of protein quality.

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Section: Resultsmentioning

confidence: 99%

Section: Dl-amino Acid Purification and Separation Analysis By Reversmentioning

confidence: 99%

The Impact of Processing on Amino Acid Racemization and Protein Quality in Processed Animal Proteins of Poultry Origin

Bellagamba

Caprino

Mentasti

et al. 2015

Italian Journal of Animal Science

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“…However, the generation of the D-amino acids during hydrolysis was not linear and not suitable in most cases. [20]. By using the DCl/D 2 O hydrolysis, the D-amino acids generated during hydrolysis are deuterated and easily distinguished from non-deuterated D-amino acids by MS.…”

Section: Establishment Of An Enantioselective Two-dimensional Hplc-msmentioning

confidence: 99%

“…Peptide or protein samples are hydrolyzed using DCl/D 2 O, resulting in the formation of "deuterated" amino acids at their α position during the chemical racemization [20][21].…”

Section: Introductionmentioning

confidence: 99%

Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Ishigo

Negishi²,

Miyoshi

et al. 2015

Chromatography

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A two-dimensional (2D) HPLC-MS/MS method has been established for the determination of trace amounts of D-amino acid residues in proteins. D-Amino acid residues are now increasingly recognized as biomarkers of diseases and key moieties for the regulation of protein structures/functions, therefore, a sensitive analytical method is highly required. However, non-negligible amounts of D-amino acids are produced by chemical racemization during the hydrolysis of proteins, and a sensitive determination of D-amino acid residues is normally difficult. In the present study, DCl/D 2 O hydrolysis is adopted and the produced deuterated D-amino acids are distinguished from naturally-occurring D-amino acids in the proteins using the 2D-HPLC-MS/MS system. D-Ala, D-Asp, D-Glu, D-Pro and D-Ser (frequently observed D-amino acids in higher animals) were selected as the targets, and the sensitive determination (around 1% or less of the L-forms) could be carried out. As an application, the D-amino acid residues in ovalbumin (OVA) were determined, and the presence of a significant amount of D-Ser (1.8% of L-Ser) was demonstrated.

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“…Realization of more exact D/L-analysis, which eliminates racemization generated by hydrolysis, was demonstrated [30] and subsequently optimized [31]. Hydrolysis should be performed in deuterated solvents, usually in deuterated hydrochloric acid [30,32,33]. Any molecule that is inverted during this step automatically becomes labeled with deuterium and thus, differing by one mass unit, is detected by MS.…”

Section: D/l Amino Acid Ratio As a Tool For The Determination Of Age mentioning

confidence: 99%

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

2016

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Abstract:Occurrence of D-amino acids in living organisms is a useful indicator of various changes, diseases, or disorders. Determination of amino acid enantiomers, namely the enantiomeric ratio of amino acids or excess of certain D-amino acids, represents a useful tool in the studies of aging processes or biomarkers in disease/disorder diagnosis in humans. The amount of D-amino acids is usually very low. Therefore, suitable sample pretreatment, often derivatization, and highly selective and sensitive separation methods are essential for D-amino acid analysis in this field. Chromatographic techniques offer appropriate choices for solving these tasks. This review covers the advances in methodology and development of improved instrumental chromatographic methods focused on D,L-amino acid separation and determination. New findings in the area of possible D-amino acid biomarkers are also included.

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Determination of d-amino acids by deuterium labelling and selected ion monitoring

Cited by 84 publications

References 15 publications

The Impact of Processing on Amino Acid Racemization and Protein Quality in Processed Animal Proteins of Poultry Origin

The Impact of Processing on Amino Acid Racemization and Protein Quality in Processed Animal Proteins of Poultry Origin

Establishment of a Two-Dimensional HPLC-MS/MS Method Combined with DCl/D<sub>2</sub>O Hydrolysis for the Determination of Trace Amounts of D-Amino Acid Residues in Proteins

Enantiomeric Ratio of Amino Acids as a Tool for Determination of Aging and Disease Diagnostics by Chromatographic Measurement

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