Chromatographic determination of L- and D-amino acids in plants

Brückner, Hans; Westhauser, T.

doi:10.1007/s00726-002-0322-8

Cited by 134 publications

(83 citation statements)

References 31 publications

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“…In our previous study, we found that L-amino acid conjugates could be transported in the phloem of plants mainly by means of transporters of L-amino acids. 25 D-amino acids are rarely known to be found in higher plants, 28 so we hypothesized that D-amino acid conjugates might not be phloem mobile. Unexpectedly, D-amino acid conjugates actually exhibited obvious phloem mobility.…”

Section: Predicting the Phloem Mobility Of Test Compounds Using The Kmentioning

confidence: 99%

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The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

Zhu

Hsiang

et al. 2019

Pest Management Science

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BACKGROUND Conjugating an amino acid onto existing fungicidal parent structures has been demonstrated to be an effective way to endow non‐phloem mobile fungicides with phloem mobility. To alter the systemicity of the fungicide PCA (phenazine‐1‐carboxylic acid), 10 amino acids derivatives of this fungicide were designed and synthesized, and their synthesis, characterization, phloem and xylem mobility in Ricinus communis L, and their fungicidal activity in vitro are described. RESULTS The systemicity experiments in Ricinus communis system demonstrated that all conjugates exhibited obvious phloem mobility compared with non‐phloem‐mobile PCA, and the introduction of an L‐amino acid to PCA more greatly enhanced the phloem mobility. The five D‐amino acid conjugates exhibited higher xylem mobility than that of PCA and of each corresponding L‐amino acid conjugate. Most conjugates were found to exhibit moderate in vitro fungicidal activities against six pathogenic fungi, which were lower than that of PCA. The results of the bioassay showed fungicidal activities of PCA‐amino acid conjugates associated not only with different amino acids, but also with their conformation. Conjugation with D‐amino acid contributed to the in vitro fungicidal activities of PCA‐amino acid conjugates. CONCLUSIONS The current research offers a new strategy for enhancing the systemicity of non‐phloem‐mobile fungicides and presents some useful information on the effects of introducing amino acids of different steric configurations on the fungicidal activity, phloem and xylem mobility of the parent fungicide. © 2019 Society of Chemical Industry

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Section: Predicting the Phloem Mobility Of Test Compounds Using The Kmentioning

confidence: 99%

“…25 However, to our knowledge, except for glycine which has no steric configuration, almost all amino acids in higher plants are L-type. 28 Whether the steric configuration of amino acids conjugated with PCA might affect the systemicity and fungicidal activity of PCA requires further study.…”

Section: Introductionmentioning

confidence: 99%

The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

Zhu

Hsiang

et al. 2019

Pest Management Science

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“…The A. thaliana d-AAT studied in this report demonstrates broad substrate specificity, with d-Glu and d-Ala being high-affinity substrates. The various d-amino acids found in most plants [37] may be formed by the activity of homologous d-AATs that metabolize exogenous (and endogenous) d-amino acids to generate other d-amino acids. However, determination of the localization and physiological function of these other d-amino acids requires further research.…”

Section: D-amino Acids In a Thalianamentioning

confidence: 99%

Cloning and functional characterization of Arabidopsis thaliana d‐amino acid aminotransferase – d‐aspartate behavior during germination

et al. 2008

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The understanding of d‐amino acid metabolism in higher plants lags far behind that in mammals, for which the biological functions of these unique amino acids have already been elucidated. In this article, we report on the biochemical behavior of d‐amino acids (particularly d‐Asp) and relevant metabolic enzymes in Arabidopsis thaliana. During germination and growth of the plant, a transient increase in d‐Asp levels was observed, suggesting that d‐Asp is synthesized in the plant. Administration of d‐Asp suppressed growth, although the inhibitory mechanism responsible for this remains to be clarified. Exogenous d‐Asp was efficiently incorporated and metabolized, and was converted to other d‐amino acids (d‐Glu and d‐Ala). We then studied the related metabolic enzymes, and consequently cloned and characterized A. thalianad‐amino acid aminotransferase, which is presumably involved in the metabolism of d‐Asp in the plant by catalyzing transamination between d‐amino acids. This is the first report of cDNA cloning and functional characterization of a d‐amino acid aminotransferase in eukaryotes. The results presented here provide important information for understanding the significance of d‐amino acids in the metabolism of higher plants.

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“…Furthermore, AlaAT enzymes used in this analysis were not tagged as has been done previously, which can affect enzyme activity. Finally, only L-amino acid enzymes were used in this analysis given that many plant pathways are L-enantiomer stereospecific, including shikimate, aspartate, pyruvate and glutamate [18], and that a very small percent (∼0.5–3) of the total amino acids within many plants are not of the L-type [19]. To our knowledge, this is the most comprehensive kinetic analysis of AlaAT homologues.…”

Section: Introductionmentioning

confidence: 99%

Analysis of the Enzymatic Properties of a Broad Family of Alanine Aminotransferases

et al. 2013

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Alanine aminotransferase (AlaAT) has been studied in a variety of organisms due to the involvement of this enzyme in mammalian processes such as non-alcoholic hepatocellular damage, and in plant processes such as C4 photosynthesis, post-hypoxic stress response and nitrogen use efficiency. To date, very few studies have made direct comparisons of AlaAT enzymes and fewer still have made direct comparisons of this enzyme across a broad spectrum of organisms. In this study we present a direct kinetic comparison of glutamate:pyruvate aminotransferase (GPAT) activity for seven AlaATs and two glutamate:glyoxylate aminotransferases (GGAT), measuring the KM values for the enzymes analyzed. We also demonstrate that recombinant expression of AlaAT enzymes in Eschericia coli results in differences in bacterial growth inhibition, supporting previous reports of AlaAT possessing bactericidal properties, attributed to lipopolysaccharide endotoxin recognition and binding. A probable lipopolysaccharide binding region within the AlaAT enzymes, homologous to a region of a lipopolysaccharide binding protein (LBP) in humans, was also identified in this study. The AlaAT enzyme differences identified here indicate that AlaAT homologues have differentiated significantly and the roles these homologues play in vivo may also have diverged significantly. Specifically, the differing kinetics of AlaAT enzymes and how this may alter the nitrogen use efficiency in plants is discussed.

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Chromatographic determination of L- and D-amino acids in plants

Cited by 134 publications

References 31 publications

The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

The influence of steric configuration of phenazine‐1‐carboxylic acid‐amino acid conjugates on fungicidal activity and systemicity

Cloning and functional characterization of Arabidopsis thaliana d‐amino acid aminotransferase – d‐aspartate behavior during germination

Analysis of the Enzymatic Properties of a Broad Family of Alanine Aminotransferases

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