Production of tartrates by cyanide-mediated dimerization of glyoxylate: a potential abiotic pathway to the citric acid cycle.

Abstract

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.

• Authors: Christopher Butch, Elizabeth D Cope, Pamela Pollet, Leslie Gelbaum, Ramanarayanan Krishnamurthy, Charles L Liotta
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 135 Issue 36 Pg. 13440-5 (Sep 11 2013) ISSN: 1520-5126 [Electronic] United States
• PMID: 23914725 (Publication Type: Journal Article, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Cyanides
• Glyoxylates
• Tartrates
• glyoxylic acid

Topics

• Citric Acid Cycle
• Cyanides (chemistry)
• Dimerization
• Glyoxylates (chemistry)
• Molecular Structure
• Tartrates (chemical synthesis, chemistry)