Production of Tartrates by Cyanide-Mediated Dimerization of Glyoxylate: A Potential Abiotic Pathway to the Citric Acid Cycle
Open accessAbstract
An abiotic formation of meso- and DL-tartrates in 80% yield via the cyanide-catalyzed dimerization of glyoxylate under alkaline conditions is demonstrated. A detailed mechanism for this conversion is proposed, supported by NMR evidence and (13)C-labeled reactions. Simple dehydration of tartrates to oxaloacetate and an ensuing decarboxylation to form pyruvate are known processes that provide a ready feedstock for entry into the citric acid cycle. While glyoxylate and high hydroxide concentration are atypical in the prebiotic literature, there is evidence for natural, abiotic availability of each. It is proposed that this availability, coupled with the remarkable efficiency of tartrate production from glyoxylate, merits consideration of an alternative prebiotic pathway for providing constituents of the citric acid cycle.
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This chemistry alternates aldol-type additions of key metabolites (pyruvate, oxaloacetate, malonate) to glyoxylate with the decarboxylation of oxalomalate and oxidative decarboxylations from HKG, malate, oxaloacetate and 3-carboxymalate.
“This chemistry alternates aldol-type additions of key metabolites (pyruvate, oxaloacetate, malonate) to glyoxylate with the decarboxylation of oxalomalate and oxidative decarboxylations from HKG, malate, oxaloacetate and 3-carboxymalate.116,117”
From The protometabolic nature of prebiotic chemistry (2023) · cites this paper as [117]
The Mechanistic Investigations section describes an aldol reaction with glyoxylate and a decarboxylation in a side pathway. It does not describe aldol additions of pyruvate, oxaloacetate, and malonate to glyoxylate, or the specified sequence of decarboxylations from oxalomalate, HKG, malate, oxaloacetate, and 3-carboxymalate. The Introduction mentions oxaloacetate and pyruvate only as potential downstream products of tartrate. (LLM, conf=0.84)
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- Authors
- Butch, C., Cope, E. D., Pollet, P., Gelbaum, L., Krishnamurthy, R., & Liotta, C. L.
- Affiliations
- Georgia Institute of Technology (US)
- Scripps Research Institute (US)
- Corresponding author
- Krishnamurthy, Ramanarayanan
- Liotta, Charles L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2013-08-30
- Volume
- 135
- Issue
- 36
- Pages
- 13440-13445
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- PMC
- PMC3777280
- OpenAlex
- W1973203893
- Cited by
- 46
- References
- 33
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- 2.16
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- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Locations
- Journal of the American Chemical Society (publishedVersion, other-oa)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Science Foundation
- National Aeronautics and Space Administration
- Division of Chemistry
- Topics
- Physical Sciences › Physics and Astronomy › Astronomy and Astrophysics › Origins and Evolution of Life
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Synthetic Organic Chemistry
- Keywords
- glyoxylic acid, cyanide catalysis, dimerization, prebiotic chemistry, TCA cycle, oxaloacetate, pyruvate, 13C labeling, reaction mechanism, alkaline conditions
- MeSH terms
- Citric Acid Cycle, Cyanides, Glyoxylates, Tartrates, Molecular Structure, Dimerization
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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