ArticleACS omega2020
Pyruvate Aldol Condensation Product: A Metabolite That Escaped Synthetic Preparation for Over a Century.
Article in ACS omega, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 19 citations in OpenAlex.
- Molecular Average and Intramolecular δAnalytical chemistry · 2025Article
- A Brand-New Metal Complex Catalyst-Free Approach to the Synthesis of 2,8-Dimethylimidazo[1,2-Molecules (Basel, Switzerland) · 2025Article
- Low-biomass pyruvate production with engineered Vibrio natriegens is accompanied by parapyruvate formation.Microbial cell factories · 2025Article
- SABRE-SHEATH Hyperpolarization of [1,5-ACS sensors · 2024Article
- Parapyruvate Induces Neurodegeneration in C57BL/6JNarl Mice via Inhibition of the α-Ketoglutarate Dehydrogenase Complex.ACS omega · 2024Article
- Enzymatic Reactions Observed with Zero- and Low-Field Nuclear Magnetic Resonance.Analytical chemistry · 2023Article
- Simultaneous magnetic resonance imaging of pH, perfusion and renal filtration using hyperpolarizedNature communications · 2023Article
- Ambient temperature CONature communications · 2023Article
- Using Taguchi Method to Determine the Optimum Conditions for Synthesizing Parapyruvate.Molecules (Basel, Switzerland) · 2022Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The homoaldol condensation product of pyruvate, 2-methyl-4-oxopent-2-enedioic acid (OMPD), has been recently implicated as a catabolic intermediate in the bacterial degradation of lignin and previously identified from other biological sources in reports ranging over 60 years. Yet, while a preparation of the pyruvate homoaldol product precursor, 4-hydroxy-4-methyl-2-oxoglutaric acid (HMOG/Parapyruvate), was first reported in 1901, there has not been a complete published synthesis of OMPD. Analyses of reaction mixtures have helped identify zymonic acid, the lactone of HMOG, as the direct precursor to OMPD. The reaction appears to proceed through an acid- or base-mediated ring opening that does not involve formal lactone hydrolysis. In addition to a preparative protocol, we provide a proposed mechanism for the formation of methylsuccinic acid that arises from the nonoxidative decarboxylation of OMPD. Finally, we calculated the relative stability of the isomers of OMPD and found Z-OMPD to be the lowest in energy. These computations also support our observations that Z-OMPD is the most abundant isomer across a range of pH values.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.