Intramolecular carbon isotopic distribution in biologically produced acetoin

Rinaldi, G. G. L.; Meinschein, W. G.; Hayes, John M.

doi:10.1002/bms.1200010609

Cited by 50 publications

(20 citation statements)

References 7 publications

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“…The oldest is the chemical and/or enzymatic degradation of the molecule, with subsequent analysis of the resulting fragments by irm-MS Monson and Hayes, 1982;Rinaldi et al, 1974;Weilacher et al, 1996). From the d 13 C of the fragments, the complete isotopic distribution can be rebuilt, assuming that all steps are quantitative or that their specific associated fractionation is known.…”

Section: Introductionmentioning

confidence: 99%

Fractionation in position-specific isotope composition during vaporization of environmental pollutants measured with isotope ratio monitoring by 13C nuclear magnetic resonance spectrometry

Julien

Parinet

Nun

et al. 2015

Environmental Pollution

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Section: Introductionmentioning

confidence: 99%

Fractionation in position-specific isotope composition during vaporization of environmental pollutants measured with isotope ratio monitoring by 13C nuclear magnetic resonance spectrometry

Julien

Parinet

Nun

et al. 2015

Environmental Pollution

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“…The 13 C-pattern of acetoin (3-hydroxy-2-butanone; see Rinaldi et al 1974 ; Fig. 4), a by-product of some alcoholic fermentations, is a classic example for the proof of a thermodynamic order in biological systems (Galimov 1985).…”

Section: Introductionmentioning

confidence: 99%

“…Nevertheless, under suitable conditions, glycolysis also takes place, obviously depending on the actual concentrations of the involved metabo- Fig. 4 13 C-pattern of acetoin (3-hydroxy-2-butanone) from fermented apple juice (Rinaldi et al 1974) and partial 13 C-pattern of phenylacetylcarbinol (1-hydroxy-1-phenyl-propane-2-one) from the incubation of pyruvate and benzaldehyde with yeast pyruvate decarboxylase, PDC (E. Zimmer and H.-L. Schmidt, unpublished). The products are formed by the transfer of enzyme-bound "active acetaldehyde" to a carbonyl compound ("acyloin reaction").…”

Section: Introductionmentioning

confidence: 99%

Fundamentals and systematics of the non-statistical distributions of isotopes in natural compounds

Schmidt

2003

Naturwissenschaften

109

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The intermolecular and intramolecular non-statistical distribution of the isotopes of the bio-elements in natural compounds must obviously be controlled by logical principles. However, a critical review of the available isotope patterns of natural compounds indicates that a previously discussed general thermodynamic order and its mechanistic foundation cannot satisfactorily explain all experimental data. In the present contribution it is shown that a partial thermodynamic order can eventually be attained for defined positions and compounds under steady-state conditions of metabolism. However, as biological systems are generally open and irreversible, many other in vivo isotope discriminations are dominated by kinetic isotope effects, even in context with reversible reactions. On the other hand, kinetic isotope effects can only become effective in vivo in combination with metabolic branching and the implied isotope shifts of the products are balanced by their relative yields. In vivo, the influences of thermodynamic and kinetic isotope effects are modulated by interferences of the actual metabolic conditions, such as the nature and kind of precursors, alternative metabolic pathways, metabolite pools and fluxes, and by reaction mechanisms. This is demonstrated by giving examples for the isotopes of hydrogen, carbon, nitrogen, oxygen and sulfur, while simultaneously the particularities of the individual elements are elaborated. The resulting general theory of the origin of non-statistical isotope distributions in biological systems permits the interpretation and prediction of isotope patterns and provides the scientific basis for the elucidation of biosyntheses and origin assignments of natural compounds.

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“…The combined, scaled effects of diffusion and carboxylation lead to photosynthetically fixed carbon and organic matter depleted in 13 C with respect to atmospheric CO 2 . Further carbon isotope discrimination occurs during lipid synthesis due to an isotopic effect that may be associated with decarboxylation in the production of acetyl CoA from pyruvate (DeNiro and Epstein, 1977;Melzer and Schmidt, 1987) and/or due to site-specific isotopic heterogeneity in pyruvate in which the carboxyl carbon is relatively enriched (Rinaldi et al, 1974;Gleixner and Schmidt, 1997).…”

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confidence: 99%

Natural Abundance Carbon Isotope Composition of Isoprene Reflects Incomplete Coupling between Isoprene Synthesis and Photosynthetic Carbon Flow

2003

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Isoprene emission from leaves is dynamically coupled to photosynthesis through the use of primary and recent photosynthate in the chloroplast. However, natural abundance carbon isotope composition (␦ 13 C) measurements in myrtle (Myrtus communis), buckthorn (Rhamnus alaternus), and velvet bean (Mucuna pruriens) showed that only 72% to 91% of the variations in the ␦ 13 C values of fixed carbon were reflected in the ␦ 13 C values of concurrently emitted isoprene. The results indicated that 9% to 28% carbon was contributed from alternative, slow turnover, carbon source(s). This contribution increased when photosynthesis was inhibited by CO 2 -free air. The observed variations in the ␦ 13 C of isoprene under ambient and CO 2 -free air were consistent with contributions to isoprene synthesis in the chloroplast from pyruvate associated with cytosolic Glc metabolism. Irrespective of alternative carbon source(s), isoprene was depleted in 13 C relative to mean photosynthetically fixed carbon by 4‰ to 11‰. Variable 13 C discrimination, its increase by partially inhibiting isoprene synthesis with fosmidomicin, and the associated accumulation of pyruvate suggested that the main isotopic discrimination step was the deoxyxylulose-5-phosphate synthase reaction.

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Intramolecular carbon isotopic distribution in biologically produced acetoin

Abstract: Abstract-The concentrations of carbon-I3 in the individual carbon atoms of 3-hydroxy-2-butanone (acetoin) from apple cider vinegar decrease with decreasing oxidation level in the sequence

Cited by 50 publications

References 7 publications

Fractionation in position-specific isotope composition during vaporization of environmental pollutants measured with isotope ratio monitoring by 13C nuclear magnetic resonance spectrometry

Fractionation in position-specific isotope composition during vaporization of environmental pollutants measured with isotope ratio monitoring by 13C nuclear magnetic resonance spectrometry

Fundamentals and systematics of the non-statistical distributions of isotopes in natural compounds

Natural Abundance Carbon Isotope Composition of Isoprene Reflects Incomplete Coupling between Isoprene Synthesis and Photosynthetic Carbon Flow

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