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DOI: 10.1055/s-0036-1588657
A Plausible Prebiotic Origin of Glyoxylate: Nonenzymatic Transamination Reactions of Glycine with Formaldehyde
Publication History
Received: 26 September 2016
Accepted after revision: 01 November 2016
Publication Date:
17 November 2016 (online)
Abstract
Glyoxylate has been postulated to be an important prebiotic building block. However, a plausible prebiotic availability of glyoxylate has not as yet been demonstrated. Herein we report the formation of glyoxylate by means of a transamination reaction between glycine and formaldehyde in water at 50 °C and 70 °C at pH 8 and 6, respectively. The reaction was followed by means of 13C NMR and high-resolution mass spectrometry employing both unlabeled and 13C-labeled reactants. Other products accompanying the transamination process include serine, sarcosine, N,N-dimethylglycine, and carbon dioxide/bicarbonate. The mechanisms for the formation of glyoxylate and accompanying products are discussed.
1 Introduction
2 Background
3 Results and Discussion
3.1 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 8
3.2 Reaction of 13C-Labeled Glycine with Formaldehyde at pH 6
3.3 Serine-Promoted Decarboxylation of Glyoxylate
4 Conclusions
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588657.
- Supporting Information
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References and Notes
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