Study of the sequential conversion of citric to itaconic to methacrylic acid in near-critical and supercritical water

Carlsson, Magnus; Habenicht, Christine; Kam, Lance C.; Antal, Michael Jerry; Bian, Nanying; Cunningham, Robert J.; Jones, Maitland

doi:10.1021/ie00032a014

Cited by 85 publications

(106 citation statements)

References 12 publications

(19 reference statements)

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“…Some of the properties of such mixtures resemble those of some Murchison meteorite components and may be of prebiotic significance (30). Under similar conditions, citric acid (as the initial reactant -in water) will decompose to many smaller compounds (31,32): many of which are also identified in this work including citramalic acid, mesaconic acid, itaconic acid, citraconic acid, and pyruvic acid. More work must be done in order to determine how applicable such high temperature/pressure mechanisms are to those of the present low temperature pyruvate syntheses of the same compounds.…”

Section: Discussionmentioning

confidence: 59%

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Cooper

Reed

Nguyen

et al. 2011

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

111

101

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Carbonaceous meteorites deliver a variety of organic compounds to Earth that may have played a role in the origin and/or evolution of biochemical pathways. Some apparently ancient and critical metabolic processes require several compounds, some of which are relatively labile such as keto acids. Therefore, a prebiotic setting for any such individual process would have required either a continuous distant source for the entire suite of intact precursor molecules and/or an energetic and compact local synthesis, particularly of the more fragile members. To date, compounds such as pyruvic acid, oxaloacetic acid, citric acid, isocitric acid, and α-ketoglutaric acid (all members of the citric acid cycle) have not been identified in extraterrestrial sources or, as a group, as part of a "one pot" suite of compounds synthesized under plausibly prebiotic conditions. We have identified these compounds and others in carbonaceous meteorites and/or as low temperature (laboratory) reaction products of pyruvic acid. In meteorites, we observe many as part of three newly reported classes of compounds: keto acids (pyruvic acid and homologs), hydroxy tricarboxylic acids (citric acid and homologs), and tricarboxylic acids. Laboratory syntheses using 13 C-labeled reactants demonstrate that one compound alone, pyruvic acid, can produce several (nonenzymatic) members of the citric acid cycle including oxaloacetic acid. The isotopic composition of some of the meteoritic keto acids points to interstellar or presolar origins, indicating that such compounds might also exist in other planetary systems.pyruvate | citrate | Murchison meteorite | Alan Hills | interstellar nitriles

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Section: Discussionmentioning

confidence: 59%

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Cooper

Reed

Nguyen

et al. 2011

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

111

101

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“…Recently, Cody et al (2001) demonstrated experimentally that metal sulfide catalysis could promote a series of hydrocarboxylation reactions highlighting a potential reaction pathway leading up from propene to hydroaconitic acid; i.e., an abiotic carbon fixation pathway that ends one oxygen atom away from citric acid. The potential utility of such a pathway lies in the fact that it is well known that under hydrothermal conditions citric acid is a prolific source of pyruvic acid (Carlsson et al, 1994;Cody et al, 2001). Pyruvic acid is a very useful prebiotic product, for example, in the presence of NH 4 ϩ a simple reductive amination reaction provides a ready source of alanine (Brandes et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

Assaying the catalytic potential of transition metal sulfides for abiotic carbon fixation

Cody

Boctor

Brandes

et al. 2004

Geochimica et Cosmochimica Acta

122

119

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“…[35][36][37][38]) and of acids (e.g. [39,40]) and the formation [41] of 5-hydroxymethyl-2-furfural (HMF).…”

Section: Fast and Slow Pyrolysismentioning

confidence: 99%

The facts and hypotheses relating to the phenomenological model of cellulose pyrolysis

Mamleev

Bourbigot

Bras

et al. 2009

Journal of Analytical and Applied Pyrolysis

193

152

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Study of the sequential conversion of citric to itaconic to methacrylic acid in near-critical and supercritical water

Cited by 85 publications

References 12 publications

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Detection and formation scenario of citric acid, pyruvic acid, and other possible metabolism precursors in carbonaceous meteorites

Assaying the catalytic potential of transition metal sulfides for abiotic carbon fixation

The facts and hypotheses relating to the phenomenological model of cellulose pyrolysis

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