Quantitative 2H NMR at Natural Abundance Can Distinguish the Pathway Used for Glucose Fermentation by Lactic Acid Bacteria

Roger, Olivier; Lavigne, Régis; Mahmoud, Mohamed H.; Buisson, Corinne; Onno, Bernard; Zhang, Ben‐Li; Robins, Richard J.

doi:10.1074/jbc.m401232200

Cited by 17 publications

(22 citation statements)

References 28 publications

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“…The data used to obtain Equations 9 -15 are quantitative and obtained under uniform conditions. Therefore, the conversion factor (C f ), which represents quantitatively the extent to which each 2 H of glucose is retained in the ethanol produced, can be calculated (2,5). This factor is dependent on the stoichiometry of the overall bioconversion (Reaction 1).…”

Section: Resultsmentioning

confidence: 99%

“…Five spectra were recorded for each sample and an exponential multiplication associated with a line broadening of 0.5 Hz was used. The quantitative measurement of the areas under the peaks and the calculation of the ( 2 H/ 1 H) i ratios were carried out as described previously (5 …”

Section: Ppm)mentioning

confidence: 99%

“…Thus, where ( 2 H/ 1 H) i is the isotopic ratio at position i of the product, ( 2 H/ 1 H) m is the isotopic ratio of the medium, and ( 2 H/ 1 H) j is the isotopic ratio at site j of the substrate. The terms a im and a ij are the isotope redistribution coefficients that give the quantitative description of the link between the substrate and the products (2,4,5). The value of these parameters is principally defined by the exchange reactions that can occur, directly or indirectly, between the water of the medium and the hydrogen atoms in the substrate, the intermediates and the products, and the kinetic isotope effects associated with the biochemical reactions involved in the fermentation pathway.…”

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Non-equivalence of Hydrogen Transfer from Glucose to the pro-R and pro-S Methylene Positions of Ethanol during Fermentation by Leuconostoc mesenteroides Quantified by 2H NMR at Natural Abundance

Robins

Petavy

Nemmaoui

et al. 2008

Journal of Biological Chemistry

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The anaerobic fermentation of glucose by Leuconostoc mesenteroides via the reductive pentose phosphate pathway leads to the accumulation of lactic acid and ethanol. The isotope redistribution coefficients (a ij ) that characterize the specific derivation of each hydrogen atom in ethanol in relation to the non-exchangeable hydrogen atoms in glucose and the medium water have been determined using quantitative 2 H NMR. First, it is confirmed that the hydrogens of the methylene group are related only to the 1 and 3 positions of glucose via the NAD(P)H pool and not to the 4 position, in contrast to ethanol produced by Saccharomyces cerevisiae. Second, it is found that the conversion factors (C f ) for the transfer of hydrogen to the pro-S and pro-R positions of the methylene group are not equivalent: the C f -1-R:C f -1-S ratio is 2.1, whereas the C f -3-R:C f -3-S ratio is 0.8. It is shown that this non-equivalence is not determined by the stereochemistry of the terminal NADH-and NADPH-dependent alcohol dehydrogenases, but is dependent on the cofactor selectivities of the reductive and oxidative steps of the reduced nucleotide cycle.

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Section: Resultsmentioning

confidence: 99%

Section: Ppm)mentioning

confidence: 99%

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confidence: 99%

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Non-equivalence of Hydrogen Transfer from Glucose to the pro-R and pro-S Methylene Positions of Ethanol during Fermentation by Leuconostoc mesenteroides Quantified by 2H NMR at Natural Abundance

Robins

Petavy

Nemmaoui

et al. 2008

Journal of Biological Chemistry

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“…In previous studies, we have shown by isotopic quantitative 2 H NMR spectrometry that the isotopic fractionation in 2 H is distinctive depending on whether the Embden-Meyerhof-Parnas (EMP) 3 pathway or the reductive pentose phosphate (RPP) pathway is used and that the hydrogen atoms in the product can be linked to the positions in the substrate (1,2).…”

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confidence: 99%

Nonstatistical 13C Distribution during Carbon Transfer from Glucose to Ethanol during Fermentation Is Determined by the Catabolic Pathway Exploited

Bayle

Akoka

Remaud

et al. 2015

Journal of Biological Chemistry

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Background: Different fermentation pathways should lead to distinctive isotope patterns in the products. Results: Three pathways for glucose catabolism show discrete isotope patterns in ethanol. Conclusion: Catabolism by different enzyme sequences leads to differential isotope redistribution patterns. Significance: Learning how isotope fractionation occurs in nature is crucial for interpreting fractionation during biochemical and physical processes for traceability.

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“…Likewise, it can provide evidence to distinguish between different pathways to obtain the same product (9,10).…”

Section: Significancementioning

confidence: 99%

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

Romek

Nun

Remaud

et al. 2015

Proc. Natl. Acad. Sci. U.S.A.

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Tramadol, previously only known as a synthetic analgesic, has now been found in the bark and wood of roots of the African medicinal tree Nauclea latifolia. At present, no direct evidence is available as to the biosynthetic pathway of its unusual skeleton. To provide guidance as to possible biosynthetic precursors, we have adopted a novel approach of retro-biosynthesis based on the position-specific distribution of isotopes in the extracted compound. Relatively recent developments in isotope ratio monitoring by 13 C NMR spectrometry make possible the measurement of the nonstatistical position-specific natural abundance distribution of 13 C (δ 13 C i ) within the molecule with better than 1‰ precision. Very substantial variation in the 13 C positional distribution is found: between δ 13 C i = −11 and −53‰. Distribution is not random and it is argued that the pattern observed can substantially be interpreted in relation to known causes of isotope fractionation in natural products. Thus, a plausible biosynthetic scheme based on sound biosynthetic principals of precursorsubstrate relationships can be proposed. In addition, data obtained from the 18 O/ 16 O ratios in the oxygen atoms of the compound add support to the deductions made from the carbon isotope analysis. This paper shows how the use of 13 C NMR at natural abundance can help with proposing a biosynthetic route to compounds newly found in nature or those difficult to tackle by conventional means.NMR spectrometry | position-specific isotope analysis | retro-biosynthesis | tramadol | Nauclea latifolia

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Quantitative 2H NMR at Natural Abundance Can Distinguish the Pathway Used for Glucose Fermentation by Lactic Acid Bacteria

Cited by 17 publications

References 28 publications

Non-equivalence of Hydrogen Transfer from Glucose to the pro-R and pro-S Methylene Positions of Ethanol during Fermentation by Leuconostoc mesenteroides Quantified by 2H NMR at Natural Abundance

Non-equivalence of Hydrogen Transfer from Glucose to the pro-R and pro-S Methylene Positions of Ethanol during Fermentation by Leuconostoc mesenteroides Quantified by 2H NMR at Natural Abundance

Nonstatistical 13C Distribution during Carbon Transfer from Glucose to Ethanol during Fermentation Is Determined by the Catabolic Pathway Exploited

A retro-biosynthetic approach to the prediction of biosynthetic pathways from position-specific isotope analysis as shown for tramadol

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