Citric acid (2,4-13C2)

Catalog Number	ACM121633509
CAS	121633-50-9
Structure
Synonyms	Citric acid-2,4-13C2; Citric acid-[2,4-13C2]
IUPAC Name	2-hydroxy(1,3-13C2)propane-1,2,3-tricarboxylic acid
Molecular Weight	194.11
Molecular Formula	13C2C4H8O7
InChI	InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/i1+1,2+1
InChI Key	KRKNYBCHXYNGOX-ZDOIIHCHSA-N
Melting Point	153-159 °C (307-318 °F) (lit.)
Purity	98%
Solubility	Water: 383 g/L at 25°C (77 °F)
Appearance	White crystalline solid
Chemical Formula	HOC(COOH)(*CH2COOH)2
Isomeric SMILES	[13CH2](C(=O)O)C([13CH2]C(=O)O)(C(=O)O)O
Isotopic Enrichment	99 atom % 13C
pH	1.8 at ca.50 g/L at °C (77 °F)
Stability	Stable if stored under recommended conditions.
CAS (Unlabeled)	77-92-9

Case Study

Citric Acid-2,4-13C2 for in vitro Staphylococcal Ferritin B Biosynthesis

Cheung J, et al. Molecular microbiology, 2009, 74(3), 594-608.

This work used purified recombinant Sbn (siderophore biosynthesis) enzymes and constituent substrates to recapitulate staphylococcal ferritin B NIS biosynthesis in vitro. In reactions containing constituent substrates L-2,3-diaminopropionic acid, citric acid, and α-ketoglutarate, SbnCEF synthase and decarboxylase SbnH were necessary and sufficient to produce staphylococcal ferritin B. In addition, a series of enzyme reactions were analyzed by liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) to identify mass ions corresponding to biosynthetic intermediates to investigate the biosynthetic pathway of staphylococcal ferritin B.
Citric acid-2,4-13C2 for biosynthetic intermediate study
SbnH facilitates the PLP-dependent decarboxylation of the citryl-Dap intermediate. Upon adding SbnH to reactions containing SbnE, citric acid, and Dap, an [M-H]- ion at m/z 233.1 was detected, supporting the proposed decarboxylation process to yield [4]. In experiments using citric acid-2,4-13C2 instead of regular citric acid, the [M-H]- ion at m/z 233.1 was absent and shifted up by two mass units. The emergence of an SB-intermediate at [M-H]- m/z 235.1 was challenging to observe in HEPES-buffered reactions due to its overlap with the deprotonated form of HEPES, which produces two predominant mass ions at 237.1 and 235.1. To address this issue, reactions were also conducted in phosphate buffer at pH 7.4. In this buffer, the shift from 233.1 to 235.1 upon substituting citrate with citrate-2,4-13C2 became clear, as there was no background interference in this spectral region.

Citric Acid-2,4-13C2 for Tricarboxylic Acid Cycle Metabolic Network Study

Mailloux R J, et al. PloS one, 2007, 2(8), e690.

Not only does the tricarboxylic acid (TCA) cycle dominate the production of pro-oxidant NADH, but the TCA metabolic complex is an active part of the organism's oxidative defence mechanism. In this article, on the basis of Pseudomonas fluorescens and HepG2 cell lines as paradigms, it showed that the TCA cycle could be modulated to manage intracellular ROS. 13C2-2,4-citric acid was used in important analytical methods like 13C-NMR and HPLC analysis to investigate metabolic characters observed under oxidative stress.
13C2-2,4-Citrate for metabolite analysis
· Panel A displays 13C-NMR analyses of citrate fermentation end-products (CFE) from Pseudomonas fluorescens cultivated in a defined medium with citrate as the sole carbon source. Two experimental conditions were employed: I) with 13C2-2,4-citrate and NAD as substrates, and II) with the same substrates.
· Panel B presents an analysis of α-ketoglutarate (α-KG) and succinate levels in the cytosol and mitochondria of HepG2 cells exposed to various treatments: control (A), aluminum citrate (Al-citrate) (B), Al-treated cells with 5 mM α-KG supplementation (C), and control cells exposed to Al-citrate (D). Samples were acid-extracted and analyzed by HPLC.
· Panel C shows representative chromatographs illustrating citrate consumption in isolated HepG2 mitochondria. Mitochondria were isolated after a 24-hour exposure to either citrate or Al-citrate and incubated for 1 hour at 37°C in a phosphate buffer containing 1 mM citrate and 0.1 mM NAD.
· Panel D presents proton-decoupled 13C-NMR spectra obtained from HepG2 cells incubated with 10 mM 13C2-2,4-citrate for 24 hours. Cells were exposed to either citrate or Al-citrate for 24 hours and subsequently isolated for 13C-NMR analysis.

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Citric acid (2,4-13C2) (121633-50-9)

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