L'action de l'acide chlorhydrique sur l'acide pyruvique. (<i>Premier Mémoire</i>)

Jong, A. W. K. de

doi:10.1002/recl.19010200303

Cited by 12 publications

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“…When synthesized 18 (see Methods for details) from selectively 13 C-labelled [1- 13 C]pyruvic acid, ZA bears two 13 C NMR-active spin ½ nuclei and is suitable for long-term storage. In aqueous solution, ZA slowly hydrolyses to parapyruvate (PP) with a half-life of ∼2.5 h ( Supplementary Fig.…”

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confidence: 99%

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Imaging of pH in vivo using hyperpolarized 13C-labelled zymonic acid

et al. 2017

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Natural pH regulatory mechanisms can be overruled during several pathologies such as cancer, inflammation and ischaemia, leading to local pH changes in the human body. Here we demonstrate that 13C-labelled zymonic acid (ZA) can be used as hyperpolarized magnetic resonance pH imaging sensor. ZA is synthesized from [1-13C]pyruvic acid and its 13C resonance frequencies shift up to 3.0 p.p.m. per pH unit in the physiological pH range. The long lifetime of the hyperpolarized signal enhancement enables monitoring of pH, independent of concentration, temperature, ionic strength and protein concentration. We show in vivo pH maps within rat kidneys and subcutaneously inoculated tumours derived from a mammary adenocarcinoma cell line and characterize ZA as non-toxic compound predominantly present in the extracellular space. We suggest that ZA represents a reliable and non-invasive extracellular imaging sensor to localize and quantify pH, with the potential to improve understanding, diagnosis and therapy of diseases characterized by aberrant acid-base balance.

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Section: Resultsmentioning

confidence: 99%

“…Equal amounts (v/v) of [1- 13 C]pyruvic acid and 37% hydrochloric acid were incubated for 20–30 days 18 . Optionally, 1 eq.…”

Section: Methodsmentioning

confidence: 99%

Imaging of pH in vivo using hyperpolarized 13C-labelled zymonic acid

et al. 2017

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“…This is known to form in neutral solutions of pyruvate (Montgomery & Webb, 1956). It has been synthesized (De Jong, 1901) and the 13C NMR spectrum completely assigned [C-l, 169.0 ppm; C-2, 203.6 ppm; C-3, 48.5 ppm; C-4, 73.4 ppm; C-4 methyl, 26.1 ppm; C-5, 181.7 ppm (Dr. N. E. Mackenzie, personal communication)]. It should be noted that C-2 of HMKG is not detected, which is due to the fact that the recycle time is sufficiently short to result in partial saturation of the carbonyl resonances.…”

Section: Resultsmentioning

confidence: 99%

Direct observation of the enzyme-intermediate complex of 5-enolpyruvylshikimate-3-phosphate synthase by carbon-13 NMR spectroscopy

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et al. 1989

Biochemistry

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The interaction of 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase, 4,5-dideoxyshikimate 3-phosphate (ddS3P), and [2-13C]-and [3-13C]phosphoenolpyruvate (PEP) has been examined by 13C NMR spectroscopy. Although no resonances due to a dead-end intermediate complex could be detected, an enzyme active site specific formation of pyruvate was observed. The interaction of EPSP synthase with shikimate 3-phosphate (S3P) and [2-13C]- or [3-13C]PEP has been examined by 13C NMR spectroscopy. With [2-13C]PEP, in addition to the resonances due to [2-13C]PEP and [8-13C]EPSP, new resonances appeared at 164.8, 110.9, and 107.2 ppm. The resonance at 164.8 ppm has been assigned to enzyme-bound EPSP. The resonance at 110.9 ppm has been assigned to C-8 of an enzyme-free tetrahedral intermediate of the sort originally proposed by Levin and Sprinson [Levin, J. G., & Sprinson, D. B. (1964) J. Biol. Chem. 239, 1142-1150] and recently independently observed by Anderson et al. [Anderson, K. S., Sikorski, J. A., Benesi, A. J., & Johnson, K. A. (1988) J. Am. Chem. Soc. 110, 6577-6579]. The resonance at 107.2 ppm has been assigned to an enzyme-bound intermediate whose structure is closely related to that of the tetrahedral intermediate. With [3-13C]PEP, new resonances appeared at 88.9, 26.2, 25.5, and 24.5 ppm. The resonance at 88.9 ppm has been assigned to enzyme-bound EPSP. The resonance at 26.2 ppm, which was found to correlate with 1.48 ppm by isotope-edited multiple quantum coherence 1H NMR spectroscopy, has been assigned to the methyl group 4-hydroxy-4-methylketoglutarate.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…The presence of significant levels of impurities in sodium pyruvate and pyruvic acid is well documented (1)(2)(3)(4)(5)(6)(7)(8). Under strongly acidic conditions, pyruvic acid undergoes an aldol type condensation yielding 4-hydroxy-4-methyl-2-ketoglutaric acid (parapyruvate) (1)(2)(3)(4)(5). This material occurs both as the dicarboxylic acid and as a cyclic lactone derivative.…”

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confidence: 99%