Azetidine-2-carboxylic acid in the food chain

Rubenstein, Edward; McLaughlin, Theresa; Winant, Richard C.; Sánchez, Agustı́n; Eckart, Michael D.; Krasinska, Karolina; Chien, Allis

doi:10.1016/j.phytochem.2008.11.007

Cited by 31 publications

(22 citation statements)

References 24 publications

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“…It is a constituent of the diet. Aze eludes the gatekeeping function of prolyl aminoacyl tRNA synthetases, and is misincorporated into proteins in place of proline [1], [30], [31].…”

Section: Resultsmentioning

confidence: 99%

Proline: The Distribution, Frequency, Positioning, and Common Functional Roles of Proline and Polyproline Sequences in the Human Proteome

2013

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Proline is an anomalous amino acid. Its nitrogen atom is covalently locked within a ring, thus it is the only proteinogenic amino acid with a constrained phi angle. Sequences of three consecutive prolines can fold into polyproline helices, structures that join alpha helices and beta pleats as architectural motifs in protein configuration. Triproline helices are participants in protein-protein signaling interactions. Longer spans of repeat prolines also occur, containing as many as 27 consecutive proline residues. Little is known about the frequency, positioning, and functional significance of these proline sequences. Therefore we have undertaken a systematic bioinformatics study of proline residues in proteins. We analyzed the distribution and frequency of 687,434 proline residues among 18,666 human proteins, identifying single residues, dimers, trimers, and longer repeats. Proline accounts for 6.3% of the 10,882,808 protein amino acids. Of all proline residues, 4.4% are in trimers or longer spans. We detected patterns that influence function based on proline location, spacing, and concentration. We propose a classification based on proline-rich, polyproline-rich, and proline-poor status. Whereas singlet proline residues are often found in proteins that display recurring architectural patterns, trimers or longer proline sequences tend be associated with the absence of repetitive structural motifs. Spans of 6 or more are associated with DNA/RNA processing, actin, and developmental processes. We also suggest a role for proline in Kruppel-type zinc finger protein control of DNA expression, and in the nucleation and translocation of actin by the formin complex.

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“…It is a constituent of the diet. Aze eludes the gatekeeping function of prolyl aminoacyl tRNA synthetases, and is misincorporated into proteins in place of proline [1], [30], [31].…”

Section: Resultsmentioning

confidence: 99%

Proline: The Distribution, Frequency, Positioning, and Common Functional Roles of Proline and Polyproline Sequences in the Human Proteome

2013

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“…Rubenstein et al (2009) determined ACA levels of 0.21-3.4 g/g in the molasses and dried pulp of sugar beets using HPLC-tandem MS, which were much lower ACA levels than observed for P. sibiricum by our quantitative method. Among the extracts, the sample collected from Yeongwol-gun, Gangwon-do (P08) was found to contain the highest amount of ACA, whereas the sample collected from Sancheong-gun, Gyeongsangnam-do (P06) had the lowest.…”

Section: Aca Content In P Sibiricummentioning

confidence: 51%

Development of Ultra-Performance Liquid Chromatography Method Using Hydrophilic Interaction Liquid Chromatography for Quantification of Azetidine-2-Carboxylic Acid in Rhizomes of Polygonatum sibiricum F. Delaroche

Kim

Lee

Choi

et al. 2015

Journal of Liquid Chromatography & Related Technologies

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Polygonatum sibiricum F. Delaroche (P. sibiricum) is widely consumed as an ingredient in functional foods, drinking water, and tea. Its major constituent, azetidine-2-carboxylic acid (ACA), is a potent toxin that can be incorporated into proteins in place of proline, leading to protein dysfunction. Thus, quality control in the analysis of ACA in P.sibiricum is important for establishing guidelines for safe levels in foods. However, prior analyses of ACA in P. sibiricum are limited, and the few methods reported require complicated sample preparation. Here, for the quantitative analysis of ACA, we compare the traditional RPLC mode with the HILIC in HPLC. Then, we develop an ultraperformance liquid chromatography (UPLC) method to increase instrument sensitivity, using a CORTECS HILIC column. The developed method offers good linear correlation (r 2 > 0.9999), excellent precision (RSD < 1.6%), and acceptable recoveries (99.26-101.33%). The LOD and LOQ were 0.13 and 0.39 g/mL, respectively. The UPLC method using the HILIC column was much simpler because pre-purification is not required for the quantification of ACA. The proposed quantitative analysis method was Downloaded by [Texas A & M International University] at 16:52 16 August 2015 2reproducible and convenient, and our results provide reference information for the quality control of P. sibiricum as a component in consumable products.

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“…2). It has been shown experimentally that Aze can be inserted by mistake into proteins in place of proline [38].…”

Section: Sugar Beet and Msmentioning

confidence: 99%

“…For the past several decades, cows' feed has been supplemented with either beet molasses or sugar beet pulp, left as a residue after the sugar has been extracted [120]. Aze has been experimentally found in three sugar beet by-products that are fed to farm animals: sugar beet molasses, and both shredded and pelleted sugar beet pulp [38]. Casein is relatively enriched in proline [121].…”

Section: Sugar Beet and Msmentioning

confidence: 99%

“…The toxicity of these products may be due to the fact that they replace coding analogues during protein synthesis. Examples include: azetidine-2-carboxylic acid (Aze), a proline analogue [37,38]; glufosinate, a glutamate analogue that is also a popular herbicide [39]; β-N-methylamino-L-alanine (BMAA), an analogue of serine [40]; and L-canavanine, a natural analogue of L-arginine that is exploited as an insecticide [41,42]. A remarkable true-life story involving a 119-day Alaskan wilderness experiment conducted by Christopher McCandless was recounted in the book Into the Wild by Jon Krakauer (later made into a popular movie) [43].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Glyphosate pathways to modern diseases VI: Prions, amyloidoses and autoimmune neurological diseases

Samsel¹,

Seneff²

2017

JBPC

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Azetidine-2-carboxylic acid in the food chain

Cited by 31 publications

References 24 publications

Proline: The Distribution, Frequency, Positioning, and Common Functional Roles of Proline and Polyproline Sequences in the Human Proteome

Proline: The Distribution, Frequency, Positioning, and Common Functional Roles of Proline and Polyproline Sequences in the Human Proteome

Development of Ultra-Performance Liquid Chromatography Method Using Hydrophilic Interaction Liquid Chromatography for Quantification of Azetidine-2-Carboxylic Acid in Rhizomes of Polygonatum sibiricum F. Delaroche

Glyphosate pathways to modern diseases VI: Prions, amyloidoses and autoimmune neurological diseases

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