Production of Tartrates by Cyanide-Mediated Dimerization of Glyoxylate: A Potential Abiotic Pathway to the Citric Acid Cycle
| العنوان: | Production of Tartrates by Cyanide-Mediated Dimerization of Glyoxylate: A Potential Abiotic Pathway to the Citric Acid Cycle |
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| المؤلفون: | Charles L. Liotta, Christopher J. Butch, Elizabeth D. Cope, Pamela Pollet, Ramanarayanan Krishnamurthy, Leslie T. Gelbaum |
| المصدر: | Journal of the American Chemical Society |
| بيانات النشر: | American Chemical Society (ACS), 2013. |
| سنة النشر: | 2013 |
| مصطلحات موضوعية: | Decarboxylation, Cyanide, Citric Acid Cycle, Glyoxylate cycle, Tartrate, 010402 general chemistry, 01 natural sciences, Biochemistry, Article, Catalysis, chemistry.chemical_compound, Colloid and Surface Chemistry, Organic chemistry, Citrate synthase, Tartrates, 2. Zero hunger, Abiotic component, Cyanides, Molecular Structure, biology, 010405 organic chemistry, Glyoxylates, General Chemistry, 0104 chemical sciences, Citric acid cycle, chemistry, biology.protein, Hydroxide, Dimerization |
| الوصف: | 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. |
| تدمد: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja405103r |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::18d553620e2f56caed16253070bea159 https://doi.org/10.1021/ja405103r |
| Rights: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....18d553620e2f56caed16253070bea159 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15205126 00027863 |
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| DOI: | 10.1021/ja405103r |